Abstract:

Materials for organic electroluminescence devices are represented by
following general formula [1]:
##STR00001## wherein A represents a chrysene group, X1 to X4
each independently represent a substituted or unsubstituted arylene group
having 6 to 30 carbon atoms, X1 and X2 may be bonded to each
other, X3 and X4 may be bonded to each other, Y1 to
Y4 each independently represent an organic group represented by
general formula [2], a to d each represent an integer of 0 to 2 and,
a+b+c+d≧0; general formula [2] being:
##STR00002## wherein R1 to R4 each independently represent
hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20
carbon atoms, a substituted or unsubstituted aryl group having 6 to 20
carbon atoms, cyano group or form a triple bond by a linkage of R1
and R2 or R3 and R4, Z represents a substituted or
unsubstituted aryl group having 6 to 20 carbon atoms and n represents 0
or 1.

Claims:

1. A material for an organic electroluminescence device represented by
formula (4): ##STR00097## wherein X1 to X4 each independently
represent a substituted or unsubstituted arylene group having 6 to 30
carbon atoms, X1 and X2 may be bonded to each other, X3
and X4 may be bonded to each other, Y1 to Y4 each
independently represent an organic group represented by formula (2), a to
d each represent an integer of 0 to 2 with the proviso that
a+b+c+d≧0; ##STR00098## wherein R1 to R4 are each
independently a hydrogen atom, a substituted or unsubstituted alkyl group
having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group
having 6 to 20 carbon atoms, cyano group or form a triple bond by a
linkage of R1 and R2 or R3 and R4, Z represents a
substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and
n represents 0 or 1.

2. A dopant material for an organic electroluminescence device represented
by formula (4): ##STR00099## wherein X1 to X4 each
independently represent a substituted or unsubstituted arylene group
having 6 to 30 carbon atoms, X1 and X2 may be bonded to each
other, X3 and X4 may be bonded to each other, Y1 to
Y4 each independently represent an organic group represented by
formula (2), a to d each represent an integer of 0 to 2 with the proviso
that a+b+c+d≧0; ##STR00100## wherein R1 to R4 are each
independently a hydrogen atom, a substituted or unsubstituted alkyl group
having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group
having 6 to 20 carbon atoms, cyano group or form a triple bond by a
linkage of R1 and R2 or R3 and R4, Z represents a
substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and
n represents 0 or 1.

3. A hole-transporting material for an organic electroluminescence device
represented by formula (4): ##STR00101## wherein X1 to X4 each
independently represent a substituted or unsubstituted arylene group
having 6 to 30 carbon atoms, X1 and X2 may be bonded to each
other, X3 and X4 may be bonded to each other, Y1 to
Y4 each independently represent an organic group represented by
formula (2), a to d each represent an integer of 0 to 2 with the proviso
that a+b+c+d≧0; ##STR00102## wherein R1 to R4 are each
independently a hydrogen atom, a substituted or unsubstituted alkyl group
having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group
having 6 to 20 carbon atoms, cyano group or form a triple bond by a
linkage of R1 and R2 or R3 and R4, Z represents a
substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and
n represents 0 or 1.

4. The material for an electroluminescence device according to claim 1,
wherein in formula (4) a+b+c+d=0.

5. The dopant material for an electroluminescence device according to
claim 2, wherein in formula (4) a+b+c+d=0.

6. The hole-transporting material for an electroluminescence device
according to claim 3, wherein in formula (4) a+b+c+d=0.

7. A material for a blue-light emitting organic electroluminescent device
comprising the material of claim 1.

Description:

REFERENCE TO PRIOR APPLICATIONS

[0001]This application is a Continuation of U.S. application Ser. No.
11/344,604, filed Feb. 1, 2006; which is a Continuation of U.S.
application Ser. No. 10/814,121, filed Apr. 1, 2004, now abandoned; which
is a Division of U.S. application Ser. No. 09/623,057, now patented;
which is a 371 of PCT/JP99/07390, filed Dec. 28, 1999.

TECHNICAL FIELD

[0002]The present invention relates to materials for organic
electroluminescence devices which are used as a light source such as a
planar light emitting member of televisions and a back light of displays,
exhibit high efficiency of light emission and have excellent heat
resistance and a long life, organic electroluminescence devices using the
materials, novel compounds and processes for producing materials for
electroluminescence devices.

BACKGROUND ART

[0003]Electroluminescence (EL) devices using organic compounds are
expected to be used for inexpensive full color display devices of the
solid light emission type which can display a large area and development
thereof has been actively conducted. In general, an EL device is
constituted with a light emitting layer and a pair of electrodes faced to
each other at both sides of the light emitting layer. When a voltage is
applied between the electrodes, electrons are injected at the side of the
cathode and holes are injected at the side of the anode. The electrons
are combined with the holes in the light emitting layer and an excited
state is formed. When the excited state returns to the normal state, the
energy is emitted as light.

[0004]Heretofore, organic EL devices require higher driving voltages and
show inferior luminance of emitted light and inferior efficiencies of
light emission in comparison with inorganic devices. Moreover, properties
of organic EL devices deteriorate very rapidly. Therefore, heretofore,
organic EL devices have not been used practically. Although the
properties of organic EL devices have been improved, organic EL devices
exhibiting a sufficient efficiency of light emission and having
sufficient heat resistance and life have not been obtained. For example,
a phenylanthracene derivative which can be used for EL devices is
disclosed in Japanese Patent Application Laid-Open No. Heisei 8
(1996)-12600. However, an organic EL device using this compound exhibited
an efficiency of light emission as low as about 2 to 4 cd/A and
improvement in the efficiency is desired. In Japanese Patent Application
Laid-Open No. Heisei 8 (1996)-199162, an EL device having a light
emitting layer containing a fluorescent dopant of a derivative of an
amine or a diamine is disclosed. However, this EL device has a life as
short as 700 hours at an initial luminance of emitted light of 300
cd/m2 although the efficiency of light emission is 4 to 6 dc/A and
improvement in the life is desired. In Japanese Patent Application
Laid-Open No. Heisei 9 (1997)-268284, a material for EL devices having
phenylanthracene group is disclosed. This material exhibits a marked
decrease in the luminance of emitted light when the material is used at a
high temperature for a long time and heat resistance is insufficient.
Moreover, these devices do not emit light in the region of orange to red
color. Since emission of red color is indispensable for the full color
display by an EL device, a device emitting light in the region of orange
to red color is desired. When these materials are used as the host
material and other compounds are used as the doping material, a long life
cannot be obtained. It is necessary for practical use that an initial
luminance of emitted light of 10,000 d/m2 or greater be exhibited.
However, this value has not been achieved. In Japanese Patent Application
Laid-Open No. Heisei 11 (1999)-152253, an example is disclosed in which a
material for organic EL devices having a binaphthalene structure is added
to a light emitting layer having the property to transfer electrons such
as a layer of an aluminum complex or the like. However, in this example,
the aluminum complex or the like emits light and the material for organic
EL devices does not function as the light emitting center since the
energy gap of the light emitting layer of the aluminum complex or the
like is smaller than the energy gap of the material for organic EL
devices.

[0005]Synthesis of arylamines used as a material for organic EL devices
has been conducted by the Ullmann reaction using an amine and an
iodobenzene. It is described, for example, in Chem. Lett., pp. 1145 to
1148, 1989; the specification of U.S. Pat. No. 4,764,625; and Japanese
Patent Application Laid-Open No. Heisei 8 (1996)-48974 that a
triarylamine is produced by the reaction of a corresponding iodobenzene
and a diarylamine in an inert hydrocarbon solvent such as decaline at
150° C. or higher in the presence of one equivalent or more of
copper powder and a base such as potassium hydroxide as the typical
example.

[0006]However, the process using the Ullmann reaction has drawbacks in
that an expensive iodide must be used as the reacting agent, that the
reaction cannot be applied to many types of compounds, that the yield of
the reaction is not sufficient, that the reaction requires a temperature
as high as 150° C. and a long time and that waste liquid
containing a great amount of copper is formed since copper powder is used
in a great amount and environmental problems arise.

DISCLOSURE OF THE INVENTION

[0007]The present invention has been made to overcome the above problems
and has an object to provide a material for organic electroluminescence
devices, an organic electroluminescence device and a novel compound which
exhibit high efficiency of light emission and have a long life and
excellent heat resistance and a process for producing the material for
organic electroluminescence devices.

[0008]As the result of extensive studies by the present inventors to
develop the material for organic EL devices having the advantageous
properties described above and an organic EL device using the material,
it was found that the object can be achieved by using the compounds
represented by general formulae [1] and [3] to [10] which are shown
below. The present invention has been completed based on this knowledge.

[0009]It was also found by the present inventors that the above object can
be achieved by using the compounds represented by general formulae [11]
and [11'] as the doping material or the light emitting center.

[0010]It was further found by the present inventors that a tertiary
arylamine which is a material for organic EL devices can be synthesized
with a high activity by the reaction of an amine and an aryl halide in
the presence of a catalyst comprising a phosphine compound and a
palladium compound and a base. The present invention has been completed
based on the above knowledge.

[0011]The material for organic electroluminescence devices (referred to as
the material for organic EL devices) of the present invention is a
compound represented by following general formula [1]:

##STR00003##

wherein A represents a substituted or unsubstituted arylene group having
22 to 60 carbon atoms, X1 to X4 each independently represent a
substituted or unsubstituted arylene group having 6 to 30 carbon atoms,
X1 and X2 may be bonded to each other, X3 and X4 may
be bonded to each other, Y1 to Y4 each independently represent an
organic group represented by general formula [2], a to d each represent
an integer of 0 to 2 and, when the arylene group represented by A has 26
or less carbon atoms, a+b+c+d>0 and the arylene group does not contain
two or more anthracene nuclei; general formula [2] being:

##STR00004##

wherein R1 to R4 each independently represent hydrogen atom, a
substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a
substituted or unsubstituted aryl group having 6 to 20 carbon atoms or
cyano group or form a triple bond by a linkage of R1 and R2 or
R3 and R4, Z represents a substituted or unsubstituted aryl
group having 6 to 20 carbon atoms and n represents 0 or 1.

[0012]The material for organic electroluminescence devices of the present
invention may also be a compound represented by following general formula
[3]:

##STR00005##

wherein B represents a substituted or unsubstituted arylene group having 6
to 60 carbon atoms, X1 to X4 each independently represent a
substituted or unsubstituted arylene group having 6 to 30 carbon atoms,
X1 and X2 may be bonded to each other, X3 and X4 may
be bonded to each other, Y1 to Y4 each independently represent
an organic group represented by general formula [2] described above, a to
d each represent an integer of 0 to 2 and at least one of groups
represented by B, X1, X2, X3 and X4 has a chrysene
nucleus.

[0013]It is preferable that general formula [3] means following general
formula [4], general formula [5] or general formula [6].

##STR00006##

wherein X1 to X4, Y1 to Y4 and a to d are each
independently the same as those in general formula [3].

##STR00007##

wherein B, X1, X2, Y1, Y2, a and b are each
independently the same as those in general formula [3].

##STR00008##

wherein B, X1, X2, Y1, Y2, a and b are each
independently the same as those in general formula [3].

[0014]The material for organic electroluminescence devices of the present
invention may also be a compound represented by following general formula
[7]:

##STR00009##

wherein D represents a divalent group having a tetracene nucleus or a
pentacene nucleus, X1 to X4 each independently represent a
substituted or unsubstituted arylene group containing 6 to 30 carbon
atoms, X1 and X2 may be bonded to each other, X3 and
X4 may be bonded to each other, Y1 to Y4 each
independently represent an organic group represented by general formula
[2] described above and a to d each represent an integer of 0 to 2.

[0015]It is preferable that general formula [7] means following general
formula [8]:

##STR00010##

wherein X1 to X4, Y1 to Y4 and a to d are each
independently the same as those in general formula [7], R51 to
R60 each independently represent hydrogen atom, a substituted or
unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or
unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or
unsubstituted aryl group having 6 to 20 carbon atoms or cyano group and
adjacent groups among the groups represented by R51 to R60 may
be bonded to each other to form a saturated or unsaturated and
substituted or unsubstituted carbon ring.

[0016]The material for organic electroluminescence devices of the present
invention may also be a compound represented by following general formula
[9]:

##STR00011##

wherein E represents a divalent group comprising an anthracene nucleus
which is substituted with aryl groups or unsubstituted, X5 to
X8 each independently represent a substituted or unsubstituted
arylene group having 6 to 20 carbon atoms, X5 and X6 may be
bonded to each other, X7 and X8 may be bonded to each other,
Y1 to Y4 each independently represent an organic group
represented by general formula [2], a to d each represent an integer of 0
to 2, and when the group represented by E is an unsubstituted group:

##STR00012##

at least two of X5 to X8 contains a substituted or unsubstituted
group:

##STR00013##

[0017]The material for organic electroluminescence devices of the present
invention may also be a compound represented by following general formula
[10]:

##STR00014##

wherein Ar1 and Ar3 each independently represents a divalent
group selected from a group consisting of substituted and unsubstituted
phenylene groups, substituted and unsubstituted 1,3-naphthalene groups,
substituted and unsubstituted 1,8-naphthalene groups, substituted and
unsubstituted fluorene groups and substituted and unsubstituted biphenyl
groups, Ar2 represents a divalent group selected from a group
consisting of substituted and unsubstituted anthracene nuclei,
substituted and unsubstituted pyrene nuclei, substituted and
unsubstituted phenanthrene nuclei, substituted and unsubstituted chrysene
nuclei, substituted and unsubstituted pentacene nuclei, substituted and
unsubstituted naphthacene nuclei and substituted and unsubstituted
fluorene nuclei, X5 to X8 each independently represent a
substituted or unsubstituted arylene group having 6 to 20 carbon atoms,
X5 and X6 may be bonded to each other, X7 and X8 may
be bonded to each other, Y1 to Y4 each independently represent
an organic group represented by general formula [2] described above, a to
d each represent an integer of 0 to 2, a+b+c+d≦2, e represents 0
or 1, f represents 1 or 2 and, when Ar2 represents an anthracene
nucleus, a case in which a=b=c=d and Ar1 and Ar3 both represent
p-phenylene group is excluded.

[0018]The material for organic electroluminescence devices of the present
invention may also be a compound represented by following general formula
[11]:

##STR00015##

wherein F represents a substituted or unsubstituted arylene group having 6
to 21 carbon atoms, X1 to X4 each independently represent a
substituted or unsubstituted arylene group having 6 to 30 carbon atoms,
X1 and X2 may be bonded to each other, X3 and X4 may
be bonded to each other, Y1 to Y4 each independently represent
an organic group represented by general formula [2] described above, a to
d each represent an integer of 0 to 2, and a+b+c+d>0.

[0019]It is preferable that the group represented by F in general formula
[11] is a group represented by following general formula [12], general
formula [13] or general formula [14]:

##STR00016##

##STR00017##

wherein R5' to R24' each independently represent hydrogen atom,
a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a
substituted or unsubstituted aryl group having 6 to 20 carbon atoms or
cyano group and adjacent groups among the groups represented by R5'
to R24' may be bonded to each other to form a saturated or
unsaturated carbon ring;

##STR00018##

wherein R25' to R34' each independently represent hydrogen atom,
a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a
substituted or unsubstituted aryl group having 6 to 20 carbon atoms or
cyano group and adjacent groups among the groups represented by R5'
to R24' my be bonded to each other to form a saturated or
unsaturated carbon ring.

[0020]The material for organic EL devices of the present invention which
is represented by any of general formulae [1], [3] to [11] and [11'] can
be used also as the light emitting material for organic
electroluminescence devices.

[0021]The organic electroluminescence (EL) device of the present invention
comprises a light emitting layer or a plurality of thin films of organic
compounds comprising a light emitting layer disposed between a pair of
electrodes, wherein at least one of the thin films of organic compounds
is a layer comprising a materials for organic EL devices represented by
any of general formulae [1], [3] to [11] and [11'].

[0022]It is preferable that, in the above organic EL device, a layer
comprising the material for organic EL devices represented by any of
general formulae [1], [3] to [11] and [11] as at least one material
selected from a group consisting of a hole injecting material, a hole
transporting material and a doping material is disposed between the pair
of electrodes.

[0023]It is preferable that, in the above organic EL device, the light
emitting layer comprises 0.1 to 20% by weight of a material for organic
EL devices represented by any of general formulae [1], [3] to [11] and
[11].

[0024]It is preferable that, in the above organic electroluminescence
device, one or more materials selected from a group consisting of a hole
injecting material, a hole transporting material and a doping material
each independently comprise 0.1 to 20% by weight of the material for
organic EL devices represented by any of general formulae [1], [3] to
[11] and [11'].

[0025]It is preferable that, in the above organic EL device, the light
emitting layer is a layer comprising a stilbene derivative and a material
for organic EL devices represented by any of general formulae [1], [3] to
[11] and [11'].

[0026]In the above organic EL device, a layer comprising an aromatic
tertiary amine derivative and/or a phthalocyanine derivative is disposed
between a light emitting layer and an anode.

[0027]It is preferable that, in the above organic EL device, the energy
gap of the material for organic electroluminescence devices represented
by general formula [11] is smaller than the energy gap of a host material
by 0.07 eV or greater.

[0028]The novel compound of the present invention is represented by
following general formula [11']:

##STR00019##

wherein F represents a group represented by general formula [14], X1
to X4 each independently represent a substituted or unsubstituted
arylene group having 6 to 30 carbon atoms, X1 and X2 may be
bonded to each other, X3 and X4 may be bonded to each other,
Y1 to Y4 each independently represent an organic group
represented by general formula [2] described above, a to d represent each
an integer of 0 to 2, and a+b+c+d>0; general formula [14] being:

##STR00020##

wherein R25' to R34' each independently represent hydrogen atom,
a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a
substituted or unsubstituted aryl group having 6 to 20 carbon atoms or
cyano group and adjacent groups among the groups represented by R5'
to R24' my be bonded to each other to form a saturated or
unsaturated carbon ring.

[0029]The process for producing a material for organic EL devices of the
present invention comprises reacting, in a presence of a catalyst
comprising a phosphine compound and a palladium compound and a base, a
primary amine or a secondary amine represented by following general
formula [15]:

R(NR'H)k [15]

wherein k represents an integer of 1 to 3; when k represents 1, R and R'
represent hydrogen atom, an alkyl group or a substituted or unsubstituted
aryl group; and when k represents 2 or 3, R represents an alkylene group
or substituted or unsubstituted arylene group and R' represents hydrogen
atom, an alkyl group or a substituted or unsubstituted aryl group, with
an aryl halide represented by following general formula [16]:

Ar(X)m [16]

wherein Ar represents a substituted or unsubstituted aryl group, X
represents F, Cl, Br or I and m represents an integer of 1 to 3, and
producing a material for organic electroluminescence devices comprising
an arylamine compound.

[0030]It is preferable that the arylamine described above is a compound
represented by following general formula [17]:

##STR00021##

wherein F represents a substituted or unsubstituted arylene group having 6
to 60 carbon atoms, X1 to X4 each independently represent a
substituted or unsubstituted arylene group having 6 to 30 carbon atoms,
X1 and X2 may be bonded to each other, X3 and X4 may
be bonded to each other, Y1 to Y4 each independently represent
an organic group represented by general formula [2] described above, a to
d each represent an integer of 0 to 2, and a+b+c+d>0.

[0031]It is preferable that the phosphine compound is a trialkylphosphine
compound, a triarylphosphine compound or a diphosphine compound.

BRIEF DESCRIPTION OF THE DRAWINGS

[0032]A more complete appreciation of the invention and many of the
attendant advantages thereof will be readily obtained as the same becomes
better understood by reference to the following detailed description when
considered in connection with the accompanying drawings, wherein:

[0033]FIG. 1 shows a 1HNMR chart of compound a synthesized in
accordance with the process of the present invention.

[0034]FIG. 2 shows a 1HNMR chart of compound b synthesized in
accordance with the process of the present invention.

[0035]FIG. 3 shows a 1HNMR chart of compound e synthesized in
accordance with the process of the present invention.

THE MOST PREFERRED EMBODIMENT TO CARRY OUT THE INVENTION

[0036]In general formula [1] in the present invention, A represents a
substituted or unsubstituted arylene group having 22 to 60 carbon atoms.
Examples of the arylene group include divalent groups formed from
biphenyl, terphenyl, naphthalene, anthracene, phenanthrene, pyrene,
fluorene, thiophene, coronene and fluoranthene and divalent groups formed
by bonding a plurality of these groups to each other. X1 to X4
in general formula [1] each independently represent a substituted or
unsubstituted arylene group having 6 to 30 carbon atoms. Examples of the
group represented by X1 to X4 include monovalent or divalent
groups containing skeleton structures of phenyl, biphenyl, terphenyl,
naphthalene, anthrathene, phenanthrene, pyrene, fluorene, thiophene,
coronene and chrysene. X1 and X2 may be connected to each other
and X3 and X4 may be connected to each other.

[0037]The groups used as the substituents to the groups represented by
X1 to X4 are each independently an alkyl group having 1 to 20
carbon atoms, an alkoxy group having 1 to 20 carbon atoms or an aryl
group having 6 to 20 carbon atoms. Aryloxy groups, arylthio groups,
arylalkyl groups and aryl ketone groups are excluded from the above
substituent because compounds having the groups excluded above tend to
decompose under heating in vapor deposition and the life of the obtained
device is short.

[0038]In general formula [1], a to d each represent an integer of 0 to 2.
However, when the group represented by A has 26 or less carbon atoms,
a+b+c+d>0 and the group represented by A does not contain 2 or more
anthracene nuclei.

[0040]In general formula [2] in the present invention, Z represents a
substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
Examples of the group represented by Z include aryl groups such as phenyl
group, biphenyl group, terphenyl group, naphthyl group, anthryl group,
phenanthryl group, fluorenyl group, pyrenyl group and thiophene group.
The above aryl groups may have substituents. Examples of the substituent
include alkyl groups and aryl groups described above as the examples of
the group represented by R1 to R4, alkoxy groups, amino group,
cyano group, hydroxyl group, carboxylic acid group, ether group and ester
groups. In general formula [2], n represents 0 or 1.

[0041]As described above, since the compound represented by general
formula [1] in the present invention has a diamine structure at the
central portion and a styrylamine structure at end portions, the
ionization energy is 5.6 eV or smaller and holes can be easily injected.
The mobility of holes is 10-4 m2/Vs or greater. Therefore, the
compound has the excellent properties as the hole injecting material and
the hole transporting material. Due to the polyphenyl structure at the
center, the electron affinity is 2.5 eV or greater and electrons can be
easily injected.

[0042]Moreover, since the structure represented by A has 22 or more carbon
atoms, an amorphous thin film can be easily formed. The glass transition
temperature is raised to 100° C. or higher and heat resistance can
be improved. When two or more anthracene groups are contained in the
structure represented by A, there is the possibility that the compound
represented by general formula [1] decomposes under heating.

[0043]Compounds having a structure in which X1 and X2 or X3
and X4 are bonded to each other through a single bond or a carbon
ring bond has elevated glass transition temperatures and show improved
heat resistance.

[0044]In the compounds represented by general formulae [3] to [6] of the
present invention, B represents a substituted or unsubstituted arylene
group having 6 to 60 carbon atoms. Examples of the group represented by B
include divalent groups formed from biphenyl, terphenyl, naphthalene,
anthracene, phenanthrene, pyrene, fluorene, thiophene, coronene and
fluoranthene and divalent groups formed by bonding a plurality of these
groups to each other. X1 to X4, Y1 to Y4 and a to d
are the same as those in general formula [1], wherein at least one of the
groups represented by B, X1, X2, X3 and X4 has a
chrysene nucleus.

[0045]As described above, since the compounds represented by general
formulae [3] to [6] in the present invention have a diamine structure at
the central portion and a styrylamine structure at end portions, the
ionization energy is 5.6 eV or smaller and holes can be easily injected.
The mobility of holes is 10-4 m2/Vs or greater. Therefore, the
compound has the excellent properties as the hole injecting material and
the hole transporting material. Due to the chrysene nucleus contained in
at least one of the groups represented by B, X1, X2, X3
and X4, durability and heat resistance are improved. Therefore,
driving for a long time is enabled and an organic EL device which can be
stored or driven at high temperatures can be obtained.

[0046]Moreover, the life of the organic EL device can be extended when the
compounds represented by general formulae [3] to [6] are used as the
doping material and the efficiency of light emission can be improved when
the compounds are used as the material of the light emitting layer.

[0047]In the compound represented by general formula [7] of the present
invention, D represents a divalent group containing a substituted or
unsubstituted tetracene nucleus or pentacene nucleus. Examples of the
group represented by D include divalent groups formed by connecting a
plurality of at least one group selected from the group consisting of
biphenyl, naphthalene, anthracene, phenanthrene, fluorene and thiophene
and the tetracene nucleus or the pentacene nucleus. X1 to X4,
Y1 to Y4 and a to d are the same as those in general formula
[1], wherein X1 and X2 may be bonded to each other and X3
and X4 may be bonded to each other.

[0048]In the compound represented by general formula [8] of the present
invention, X1 to X4, Y1 to Y4 and a to d each
independently represent the same atom and groups as those described above
in general formula [1]. R51 to R60 each independently represent
hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20
carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20
carbon atoms, a substituted or unsubstituted aryl group having 6 to 20
carbon atoms or cyano group and adjacent groups among the groups
represented by R51 to R60 may be bonded to each other to form a
saturated or unsaturated and substituted or unsubstituted carbon ring.

[0049]The groups used as the substituent in general formulae [7] and [8]
are each independently an alkyl group having 1 to 20 carbon atoms, an
alkoxy group having 1 to 20 carbon atoms or an aryl group having 6 to 20
carbon atoms. Aryloxy groups, arylthio groups, arylalkyl groups and aryl
ketone groups are excluded from the above substituent because compounds
having the groups excluded above tend to decompose under heating in vapor
deposition and the life of the obtained device is short.

[0050]As described above, the compound represented by general formula [7]
in the present invention exhibits strong fluorescence in the region of
orange to red color due to the tetracene or pentacene structure. Holes
are easily injected due to the diamine structure. When this compound is
contained in the light emitting layer, holes are easily trapped and
recombination of electrons and holes is promoted. Therefore, a light
emitting device emitting yellow color, orange color and red color in a
high efficiency can be obtained.

[0051]In particular, when the compound represented by general formula [7]
is used as the doping material, the obtained light emitting device has a
long life and exhibits more excellent stability than that exhibited by
any conventional devices.

[0052]In the compound represented by general formula [9] in the present
invention, E represents a divalent group comprising an anthracene nucleus
which is substituted with aryl groups or unsubstituted. X5 to
X8 each independently represent a substituted or unsubstituted
arylene group having 6 to 20 carbon atoms. Examples of the group
represented by X5 to X8 include monovalent and divalent groups
containing the skeleton structure of phenylene, biphenyl, terphenyl,
naphthalene, anthracene, phenanthrene, fluorene and thiophene. X5
and X6 may be bonded to each other and X7 and X8 may be
bonded to each other. Y1 to Y4 and a to d are the same as those
in general formula [1].

[0053]However, when E represents an unsubstituted group:

##STR00022##

at least two of X5 to X8 contain a substituted or unsubstituted
group:

##STR00023##

[0054]As described above, since the compound represented by general
formula [9] in the present invention has a diamine structure, the
ionization energy is 5.6 eV or smaller and holes can be easily injected.
The mobility of holes is 10-4 m2/Vs or greater. Therefore, the
compound has the excellent properties as the hole injecting material and
the hole transporting material. Due to the substituted or unsubstituted
anthracene nucleus at the center, electrons are easily injected.

[0055]When the anthracene nucleus represented by E is unsubstituted, the
glass transition temperature is as low as 100° C. or lower. The
glass transition temperature can be elevated by bonding at least two
substituents and preferably 2 to 4 substituents to the nucleus as
described above. The specific biphenyl structure described above enhances
solubility of the compound represented by general formula [9] and
purification can be facilitated. When phenyl group is bonded at a
position other than the above position, i.e., at the para-position, the
content of impurities increases since purification becomes difficult and
the properties of the obtained organic EL device deteriorate. By the
substitution of aryl groups as described above, formation of pairs of the
molecules by association is suppressed and the quantum efficiency of
fluorescence emission increases. Thus, the efficiency of light emission
of the organic EL device is improved.

[0056]In the compound represented by general formula [10] in the present
invention, Ar1 and Ar3 each independently represents a divalent
group selected from the group consisting of substituted and unsubstituted
phenylene groups, substituted and unsubstituted 1,3-naphthalene groups,
substituted and unsubstituted 1,8-naphthalene groups, substituted and
unsubstituted fluorene groups and substituted and unsubstituted biphenyl
groups, Ar2 represents a divalent group selected from the group
consisting of substituted and unsubstituted anthracene nuclei,
substituted and unsubstituted pyrene nuclei, substituted and
unsubstituted phenanthrene nuclei, substituted and unsubstituted chrysene
nuclei, substituted and unsubstituted pentacene nuclei, substituted and
unsubstituted naphthacene nuclei and substituted and unsubstituted
fluorene nuclei.

[0057]Examples of the divalent group include:

##STR00024## ##STR00025## ##STR00026## ##STR00027##

[0058]X5 to X8 and Y1 to Y4 each independently
represent the same groups as those described in general formula [9]. a to
d each represent an integer of 0 to 2, a+b+c+d≦2, e represents 0
or 1 and f represents 1 or 2, wherein, when Ar2 represents an
anthracene nucleus, the case in which a=b=c=d and Ar1 and Ar3
both represent p-phenylene group is excluded.

[0059]As described above, since the compound represented by general
formula [10] in the present invention has a diamine structure, the
ionization energy is 5.6 eV or smaller and holes can be easily injected.
The mobility of holes is 10-4 m2/Vs or greater. Therefore, the
compound has the excellent properties as the hole injecting material and
the hole transporting material, in particular as the light emitting
material. Due to the polyphenyl structure of the compound having the
condensed ring at the center, electrons can be easily injected.

[0060]Since the compound has both of the polyphenyl structure and the
diamine structure, a stable amorphous thin film can be formed and
exhibits excellent heat resistance due to the glass transition
temperature of 100° C. or higher. When the compound contains two
or more structures represented by general formula [2], the condition of
a+b+c+d≦2 is required because the compound decomposes under
heating in vapor deposition for formation of the thin film. When Ar2
represents an anthracene nucleus, decomposition under heating and
oxidation in vapor deposition can be prevented by the above specific
structures of Ar1 and Ar3.

[0061]In the compounds represented by general formulae [11] and [11'] in
the material for the organic EL devices and the novel compound used in
the organic EL device of the present invention, F represents a
substituted or unsubstituted arylene group having 6 to 21 carbon atoms.
Examples of the group represented by F include divalent groups formed
from biphenyl, terphenyl, naphthalene, anthracene, phenanthrene, pyrene,
fluorene, thiophene and fluoranthene.

[0062]In general formulae [11] and [11'], a to d each represent an integer
of 0 to 2, wherein a+b+c+d>0.

[0063]As described above, since the compounds represented by general
formulae [11] and [11'] in the present invention have a diamine structure
at the center and a styrylamine structure at end portions, the ionization
energy is 5.6 eV or smaller. Therefore, the property of injecting holes
into the light emitting layer is improved by adding the compound into the
light emitting layer. Moreover, the balance between electrons and holes
in the light emitting layer is improved by catching holes and the
efficiency of light emission and the life are improved. The efficiency of
light emission and the life are improved in comparison with the case in
which the light emitting layer is composed of the above compound
represented by general formula [11] or [11'] alone as the sole material
for the organic EL material. The compound having the structure in which
X1 and X2 are bonded to each other and X3 and X4 are
bonded to each other through a single bond or through a carbon ring bond
provides an elevated glass transition temperature and improved heat
resistance.

[0064]In the group represented by general formulae [12] to [14] in the
present invention, R5' to R34' each independently represent
hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20
carbon atoms, a substituted or unsubstituted aryl group having 6 to 20
carbon atoms or cyano group and adjacent groups among the groups
represented by R5' to R24' may be bonded to each other to form
a saturated or unsaturated carbon ring. Examples of the group represented
by R5' to R34' include substituted and unsubstituted alkyl
groups such as methyl group, ethyl group, propyl group, butyl group,
sec-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl
group, octyl group, stearyl group, 2-phenylisopropyl group,
trichloromethyl group, trifluoromethyl group, benzyl group,
α-phenoxybenzyl group, α,α-dimethylbenzyl group,
α,α-methylphenylbenzyl group,
α,α-ditrifluoromethylbenzyl group, triphenyl-methyl group and
α-benzyloxybenzyl group; and substituted and unsubstituted aryl
groups such as phenyl group, 2-methylphenyl group, 3-methylphenyl group,
4-methylphenyl group, 4-ethylphenyl group, biphenyl group,
4-methylbiphenyl group, 4-ethylbiphenyl group, 4-cyclohexyl-biphenyl
group, terphenyl group, 3,5-dichlorophenyl group, naphthyl group,
5-methylnaphthyl group, anthryl group and pyrenyl group.

[0065]In the following, Compounds (1) to (28) as the typical examples of
the compound represented by general formula [1], Compounds (29) to (56)
as the typical examples of the compounds represented by general formulae
[3] to [6], Compounds (57) to (74) as the typical examples of the
compound represented by general formula [7], Compounds (75) to (86) as
the typical examples of the compound represented by general formula [8],
Compounds (87) to (104) as the typical examples of the compound
represented by general formula [9], Compounds (105) to (126) as the
typical examples of the compound represented by general formula [10] and
Compounds (127) to (141) as the typical examples of the compounds
represented by general formulae [11] and [11'] are shown. However, the
present invention is not limited to these typical examples.

[0066]The compounds represented by general formulae [1], [3] to [10] of
the present invention exhibit strong fluorescence in the solid state,
have the excellent light emitting property in the electric field and show
a quantum efficiency of fluorescence emission of 0.3 or greater since the
polyphenyl structure represented by A or B and the amine structure are
connected to each other at the center of the compounds. The compounds
represented by general formulae [7] and [8] exhibit strong fluorescence
in the solid state or the dispersed state in the fluorescence region of
yellow color, orange color or red color and have an excellent light
emitting property in the electric field since the structure containing
the tetracene nucleus or the pentacene nucleus and the amine structure
are connected to each other.

[0067]The compounds represented by general formulae [1], [3] to [10] of
the present invention can be used effectively as the light emitting
material and may be used also as the hole transporting material, the
electron transporting material and the doping material since the
compounds have all of the hole injecting property from metal electrodes
or organic thin film layers, the hole transporting property, the electron
injecting property from metal electrodes or organic thin film layers and
the electron transporting property. In particular, when the compounds
represented by general formula [7] and [8] are used as the doping
material, highly efficient emission of red light can be achieved since
the compounds works as the center of recombination of electrons and
holes.

[0068]The compound represented by general formula [8] exhibits a
particularly excellent property since the arylamine and tetracene are
bonded at the specific positions.

[0069]The organic EL device of the present invention is a device in which
one or a plurality of organic thin films are disposed between an anode
and a cathode. When the device has a single layer, a light emitting layer
is disposed between an anode and a cathode. The light emitting layer
contains a light emitting material and may also contain a hole injecting
material or a electron injecting material to transport holes injected at
the anode or electrons injected at the cathode to the light emitting
material. However, it is possible that the light emitting layer is formed
with the light emitting material of the present invention alone because
the light emitting material of the present invention has a very high
quantum efficiency of fluorescence emission, excellent ability to
transfer holes and excellent ability to transfer electrons and a uniform
thin film can be formed. The organic EL device of the present invention
having a multi-layer structure has a laminate structure such as: (an
anode/a hole injecting layer/a light emitting layer/a cathode), (an
anode/a light emitting layer/an electron injecting layer/a cathode) and
(an anode/a hole injecting layer/a light emitting layer/an electron
injecting layer/a cathode). Since the compounds represented by general
formulae [1], [3] to [11], [11'] and [17] have the excellent light
emitting property and, moreover, the excellent hole injecting property,
hole transporting property, electron injecting property and electron
transporting property, the compounds can be used for the light emitting
layer as the light emitting material.

[0070]In the light emitting layer, where necessary, conventional light
emitting materials, doping materials, hole injecting materials and
electron injecting materials may be used in addition to the compounds
represented by general formulae [1], [3] to [11], [11'] and [17] of the
present invention. Deterioration in luminance and life caused by
quenching can be prevented by the multi-layer structure of the organic
EL. Where necessary, a light emitting materials, a doping materials, a
hole injecting materials and an electron injecting materials may be used
in combination. By using a doping material, luminance and the efficiency
of light emission can be improved and blue light and red light can be
emitted. The hole injecting layer, the light emitting layer and the
electron injecting layer may each have a multi-layer structure having two
or more layers. When the hole injecting layer has a multi-layer
structure, the layer into which holes are injected from the electrode is
referred to as the hole injecting layer and the layer which receives
holes from the hole injecting layer and transports holes from the hole
injecting layer to the light emitting layer is referred to as the hole
transporting layer. When the electron injecting layer has a multi-layer
structure, the layer into which electrons are injected from the electrode
is referred to as the electron injecting layer and the layer which
receives electrons from the electron injecting layer and transports
electrons from the electron injecting layer to the light emitting layer
is referred to as the electron transporting layer. These layers are each
selected and used in accordance with factors such as the energy level and
heat resistance of the material and adhesion with the organic layers or
the metal electrodes.

[0071]Examples of the material which can be used in the light emitting
layer as the light emitting material or the doping material in
combination with the compounds represented by general formulae [1], [3]
to [11], [11'] and [17] include anthracene, naphthalene, phenanthrene,
pyrene, tetracene, coronene, chrysene, fluoresceine, perylene,
phthaloperylene, naphthaloperylene, perynone, phthaloperynone,
naphthaloperynone, diphenylbutadiene, tetraphenylbutadiene, coumarine,
oxadiazole, aldazine, bisbenzoxazoline, bisstyryl, pyrazine,
cyclopentadiene, metal complexes of quinoline, metal complexes of
aminoquinoline, metal complexes of benzoquinoline, imines,
diphenylethylene, vinylanthracene, diamino-carbazole, pyrane, thiopyrane,
polymethine, merocyanine, oxinoid compounds chelated with imidazoles,
quinacridone, rubrene, stilbene derivatives and fluorescent dyes.
However, the examples of the above material are not limited to the above
compounds.

[0072]In particular, metal complexes of quinoline and stilbene derivatives
can be used in combination with the compounds represented by general
formulae [7] and [8] as the light emitting material or the doping
material in the light emitting layer.

[0073]It is essential that the content of the doping material in the light
emitting layer is greater than the content of the compound represented by
general formula [11] or [11']. It is preferable that the content is 80 to
99.9% by weight.

[0074]As the hole injecting material, a compound which has the ability to
transfer holes, exhibits excellent effect of hole injection from the
anode and excellent effect of hole injection to the light emitting layer
or the light emitting material, prevents transfer of excited components
formed in the light emitting layer into the electron injecting layer or
the electron injecting material and has an excellent ability to form a
thin film is preferable. Examples of such a compound include
phthalocyanine derivatives, naphthalocyanine derivatives, porphyrin
derivatives, oxaozole, oxadiazole, triazole, imidazole, imdazolone,
imdazolethione, pyrazoline, pyrazolone, tetrahydroimidazole, oxazole,
oxadiazole, hydrazone, acylhydrazone, polyarylalkanes, stilbene,
butadiene, benzidine-type triphenylamine, styrylamine type
triphenylamine, diamine type triphenylamine, derivatives of these
compounds and macromolecular compounds such as polyvinylcarbazole,
polysilane and conductive macromolecules. However, examples of such a
compound are not limited to the compounds described above.

[0075]Among the hole injection materials which can be used in the organic
EL device of the present invention, more effective hole injecting
materials are aromatic tertiary amine derivatives and phthalocyanine
derivatives.

[0076]Examples of the aromatic tertiary amine derivative include
triphenylamine, tritolylamine, tolyldiphenylamine,
N,N'-diphenyl-N,N'-(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine,
N,N,N',N'-(4-methylphenyl) 1,1'-phenyl-4,4'-diamine,
N,N,N',N'-(4-methylphenyl)-1,1'-biphenyl-4,4'-diamine,
N,N'-diphenyl-N,N'-dinaphthyl-1,1'-biphenyl-4,4'-diamine,
N,N'-(methylphenyl)-N,N'-(4-n-butylphenyl)phenanthrene-9,10-diamine,
N,N-bis(4-di-4-tolylaminophenyl)-4-phenylcyclohexane and oligomers and
polymers having a skeleton structure of these aromatic tertiary amines.
However, examples of the aromatic tertiary amine derivative are not
limited to the above compounds.

[0078]As the electron injecting material, a compound which has the ability
to transport electrons, exhibits excellent effect of electron injection
from the cathode and excellent effect of electron injecting to the light
emitting layer or the light emitting material, prevents transfer of
excited components formed in the light emitting layer into the hole
injecting layer or the hole injecting material and has an excellent
ability to form a thin film is preferable. Examples of such a compound
include fluorenone, anthraquinodimethane, diphenoquinone, thiopyrane
dioxide, oxazole, oxadiazole, triazole, imidazole,
peryleneteteracarboxylic acid, fluorenylidenemethane,
anthraquinodimethane, anthrone and derivatives of these compounds.
However, examples of such a compound is not limited to the compounds
described above. The electron injecting property can be improved by
adding an electron accepting material to the hole injecting material or
an electron donating material to the electron injecting material.

[0081]In the organic EL device of the present invention, at least one of
light emitting materials, doping materials, hole injecting materials and
electron injecting materials may be contained in the same layer of the
light emitting layer in addition to the compounds represented by general
formulae [1] and [3] to [8]. In order to improve stability of the organic
EL device of the present invention with respect to the temperature, the
humidity and the oxygen, a protecting layer may be formed on the entire
surface of the device or the entire device may be protected with silicon
oil or a resin.

[0082]As the conductive material used as the anode of the organic EL
device, a material having a work function of 4 eV or greater is suitable.
Examples of such a material include carbon, aluminum, vanadium, iron,
cobalt, nickel, tungsten, silver, gold, platinum, palladium, alloys of
these metals, metal oxides used for ITO substrates and NESA substrates
such as tin oxide and indium oxide and organic conductive resins such as
polythiophene and polypyrrol. As the conductive material used for the
cathode, a material having a work function smaller than 4 eV is suitable.
Examples of such a material include magnesium, calcium, tin, lead,
titanium, yttrium, lithium, ruthenium, manganese, aluminum and alloys of
these metals. However, examples of the materials used for the anode and
the cathode are not limited to the above examples. Typical examples of
the alloy include alloys of magnesium and silver, alloys of magnesium and
indium and alloys of lithium and aluminum. However, examples of the alloy
are not limited to these alloys. The composition of the alloy is
determined by the temperature of the source of vapor deposition, the
atmosphere and the degree of vacuum and a suitable composition is
selected. The anode and the cathode may have a multi-layer structure
having two or more layers, where necessary.

[0083]In the organic EL device, it is preferable that at least one face of
the device is sufficiently transparent in the wave length region of
emitted light to achieve efficient light emission. It is preferable that
the substrate is also transparent. In the preparation of the transparent
electrode, the above conductive material is used and vapor deposition or
sputtering is conducted so that the prescribed transparency is surely
obtained. It is preferable that the electrode disposed on the light
emitting face has a light transmittance of 10% or greater. The substrate
is not particularly limited as long as the substrate has mechanical
strength and strength at high temperatures and is transparent. Glass
substrates or transparent films of resins may be used. Example of the
transparent films of resins include films of polyethylene, ethylene-vinyl
acetate copolymers, ethylene-vinyl alcohol copolymers, polypropylene,
polystyrene, polymethyl methacrylate, polyvinyl chloride, polyvinyl
alcohol, polyvinyl butyral, nylon, polyether ether ketones, polsulfones,
polyether sulfones, tetrafluoroethylene-perfluoroalkyl vinyl ether
copolymers, polyvinyl fluoride, tetrafluoro-ethylene-ethylene copolymers,
tetrafluoroethylene-hexafluoropropylene copolymers,
polychlorotrifluoroethylene, polyvinylidene fluoride, polyesters,
polycarbonates, polyurethanes, polyimides, polyether imides, polyimides
and polypropylene.

[0084]Each layer of the organic EL device of the present invention can be
produced suitably in accordance with a dry process of film formation such
as vacuum vapor deposition, sputtering and plasma and ion plating or a
wet process of film formation such as spin coating, dipping and flow
coating. The thickness of the film is not particularly limited. However,
it is necessary that the thickness be set at a suitable value. When the
thickness is greater than the suitable value, a great voltage must be
applied to obtain a prescribed output of light and the efficiency
deteriorates. When the thickness is smaller than the suitable value, pin
holes are formed and a sufficient luminance cannot be obtained even when
the electric field is applied. In general, the suitable range of the
thickness is 5 nm to 10 μm. A thickness in the range of 10 nm to 0.2
μm is preferable.

[0085]When the device is produced in accordance with a wet process,
materials forming each layer are dissolved or dispersed in a suitable
solvent such as ethanol, chloroform, tetrahydrofuran and dioxane and a
film is formed from the solution or the suspension. The solvent is not
particularly limited. In any organic thin layer, suitable resins and
additives may be used to improve the property to form a film and to
prevent formation of pin holes. Examples of the resin which can be used
include insulating resins such as polystyrene, polycarbonates,
polyarylates, polyesters, polyamides, polyurethanes, polysulfones,
polymethyl methacrylate, polymethyl acrylate and cellulose, copolymers
derived from these resins, photoconductive resins such as
poly-N-vinylcarbazole and polysilane and conductive resins such as
polythiophene and polypyrrol. Examples of the additive include
antioxidants, ultraviolet light absorbents and plasticizers.

[0086]As described above, by using the compounds of the present invention
for the light emitting layer of the organic EL device, practically
sufficient luminance can be obtained under application of a low voltage.
Therefore, the organic EL device exhibiting a high efficiency of light
emission and having a long life due to suppressed degradation and
excellent heat resistance can be obtained.

[0087]The organic EL device of the present invention can be used for a
planar light emitting member such as a flat panel display of wall
televisions, a back light for copiers, printers and liquid crystal
displays, a light source of instruments, display panels and a marker
light.

[0088]The materials of the present invention can be used not only for the
organic EL devices but also in the field of electronic photosensitive
materials, opto-electric conversion devices, solar batteries and image
sensors.

[0090]Examples of the secondary amine represented by general formula [15]
include the following compounds:

##STR00061## ##STR00062##

[0091]The aryl halide represented by general formula [16] is not
particularly limited. The group represented by Ar is, in general, an
alkyl group having 1 to 18 carbon atoms or a substituted or unsubstituted
aryl group having 6 to 22 carbon atoms, The aromatic ring may have
substituents. In the present invention, the aryl group include
hydrocarbon groups having condensed rings.

[0093]Aryl halides having 2 or more halogen atoms and preferably 2 or 3
halogen atoms can also be used as long as the object of the present
invention is not adversely affected. Examples of the aryl halide having 2
or more halogen atoms include 1,2-dibromobenzene, 1,3-dibromobenzene,
1,4-dibromobenzene, 9,10-dibromoanthracene, 9,10-dichloroanthracene,
4,4'-dibromobiphenyl, 4,4'-dichlorobiphenyl, 4,4'-diiodobiphenyl,
1-bromo-2-fluorobenzene, 1-bromo-3-fluorobenzene,
1-bromo-4-fluorobenzene, 2-bromochlorobenzene, 3-bromochlorobenzene,
4-bromochlorobenzene, 2-bromo-5-chlorotoluene,
3-bromo-4-chlorobenzotrifluoride, 5-bromo-2-chlorobenzotrifluoride,
1-bromo-2,3-dichlorobenzene, 1-bromo-2,6-dichlorobenzene,
1-bromo-3,5-dichlorobenzene, 2-bromo-4-fluorotoluene,
2-bromo-5-fluorotoluene, 3-bromo-4-fluorotoluene,
4-bromo-2-fluorotoluene, 4-bromo-3-fluorotoluene,
tris(4-bromophenyl)amine, 1,3,5-tribromobenzene and the following
compounds:

##STR00065## ##STR00066##

[0094]In the process for producing materials for organic EL devices of the
present invention, the method of addition of the aryl halide is not
particularly limited. For example, two different types of aryl halides
may be mixed with a primary amine before starting the reaction and the
reaction may be conducted using the obtained mixture. Alternatively, a
primary amine may be reacted with one of two types of aryl halides. Then,
the obtained secondary amine may be added to the other aryl halide and
the reaction is conducted. The latter method in which different aryl
halides are added successively is preferable because a tertiary amine can
be produced more selectively.

[0095]The amount of the added aryl halide is not particularly limited.
When the two types of aryl halides are added to the primary amine
simultaneously, it is suitable that the amount of the aryl halide is in
the range of 0.5 to 10 moles per 1 mole of the primary amine. From the
standpoint of economy and easier treatments after the reaction such as
separation of the unreacted aryl halide, it is preferable that the amount
of the aryl halide is in the range of 0.7 to 5 moles per 1 mole of the
primary amine. When the two types of aryl halides are added successively
to the primary amine, the aryl halide which is added first is added to
the reaction system in an amount in the range of 0.5 to 1.5 moles per 1
mole of the amino group in the primary amine. From the standpoint of
improving the selectivity of the tertiary amine of the object compound,
it is preferable that the above aryl halide is added to the reaction
system in an amount of 0.9 to 1.1 mole per 1 mole of the amino group in
the primary amine.

[0096]The aryl halide which is added after preparation of the secondary
amine is added in an amount of 0.1 to 10 mole per 1 mole of the amino
group in the primary amine used as the starting material. To prevent
complicated operations in separation of the unreacted aryl halide and the
unreacted secondary amine after the reaction, it is preferable that the
aryl halide is added in an amount of 0.9 to 5 mole per 1 mole of the
amino group in the primary amine used as the starting material.

[0097]The palladium compound used as the catalyst component in the present
invention is not particularly limited as long as it is a compound of
palladium. Examples of the palladium compound include compounds of
tetravalent palladium such as sodium hexachloropalladate(IV) tetrahydrate
and potassium hexachloropalladate(IV); compounds of divalent palladium
such as palladium(II) chloride, palladium(II) bromide, palladium(II)
acetate, palladium acetylacetonate(II),
dichlorobis-(benzonitrile)palladium(II),
dichlorobis(acetonitrile)palladium(II),
dichloro(bis(diphenylphosphino)ethane)palladium(II),
dichlorobis-(triphenylphosphine)palladium(II),
dichlorotetraamminepalladium(II),
dichloro(cycloocta-1,5-diene)palladium(II) and palladium
trifluoro-acetate(II); and compounds of zero-valent palladium such as
tris(dibenzylideneacetone) dipalladium(0) (Pd2(dba)3),
chloroform complex of tris(dibenzylideneacetone) dipalladium(0),
tetrakis(triphenyl phosphine)palladium(0) and bis
is(diphenylphosphino)ethane-palladium(0). In the process of the present
invention, the amount of the palladium compound is not particularly
limited. The amount of the palladium compound is 0.00001 to 20.0% by mole
as the amount of palladium per 1 mol of the primary amine. The tertiary
amine can be synthesized with a high selectivity when the amount of the
palladium compound is in the above range. Since the palladium compound is
expensive, it is preferable that the amount of the palladium compound is
0.001 to 5.0 mole as the amount of palladium per 1 mole of the primary
amine.

[0098]In the process of the present invention, the trialkylphosphine
compound used as the catalyst component is not particularly limited.
Examples of the trialkylphosphine compound include triethylphosphine,
tricyclohexylphosphine, triisopropylphosphine, tri-n-butylphosphine,
triisobutylphosphine, tri-sec-butylphosphine and tri-tert-butylphosphine.
Among these compounds, tri-tert-butylphosphine is preferable because of
the high reaction activity. The triarylphosphine compound is not
particularly limited. Examples of the triarylphosphine include
triphenylphosphine, benzyldiphenylphosphine, tri-o-toluoylphosphine,
tri-m-toluoylphosphine and tri-p-toluoylphosphine. Among these compounds,
triphenylphosphine and tri-o-toluoylphosphine are preferable. The
diphosphine compound is not particularly limited. Examples of the
diphosphine compound include bis(dimethylphosphino)methane,
bis(dimethylphosphino)ethane, bis(dicyclohexylphosphino)methane,
bis(dicyclohexylphosphino)ethane, bis(diphenylphosphino)ethane,
1,3-bis(diphenylphosphino)propane, 1,4-bis(diphenylphosphino)butane,
bis(diphenylphosphino)ferrocene,
(R)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl((R)-BINAP),
(S)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl-((S)-BINAP),
2,2'-bis(diphenylphosphino)-1,1'-bisnaphthyl((±)-BINAP),
2S,3S-bis(diphenylphosphino)butane((S,S)-CHIRAPHOS),
2R,3R-bis(diphenylphosphino)butane((R,R)-CHIRAPHOS),
2,3-bis(diphenyl-phosphino)butane(±)-CHIRAPHOS),
(R)-2,2'-bis(di-p-toluoylphosphino)-1,1-binaphthyl((R)-Tol-BINAP),
(S)-2,2'-bis(di-p-toluoylphosphino)-1,1'-binaphthyl((S)-Tol-BINAP),
2,2'-bis(di-p-toluoylphosphino)-1,1'-bisnaphthyl((±)-Tol-BINAP),
4R,5R-bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxorane((R,R)-DIOP)-
, 4S,5S-bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxorane(S,S)-DIOP)-
, 4,5-bis(diphenyl-phosphinomethyl)-2,2-dimethyl-1,3-dixorane((±)-DIOP)-
, N,N'-dimethyl-(S)-1-[(R)-1',2-bis(diphenylphosphino)feffocenyl]ethylamin-
e((S), (R)-BPPFA),
N,N'-dimethyl-(R)-1-[(S)-1',2-bis(diphenylphosphino)ferrocenyl]-ethylamin-
e((R), (S)-BPPFA) and
N,N'-dimethyl-1-[1',2-bis(diphenyl-phosphino)ferrocenyl]ethylamine((±)-
-BPPFA). Among these compounds, bis(diphenylphosphino)ethane,
1,3-bis(diphenylphosphino)propane, bis(diphenylphosphino)ferrocene and
BINAPs are preferable. BINAPs may be either optically active compounds or
racemic compounds.

[0099]The amounts of the trialkylphosphine compound, the
triphenylphosphine compound and the diphosphine compound are 0.01 to
10,000 mole per 1 mole of the palladium compound. As long as the amounts
are in this range, the selectivity of the arylamine does not change.
However, it is preferable that the amount is 0.1 to 10 mole per 1 mol of
the palladium compound since the phosphine compounds are expensive.

[0100]In the process of the present invention, the palladium compound and
the phosphine compound are the essential components of the catalyst. The
combination of these components is added to the reaction system as the
catalyst. As the method of addition of the components, the two components
may be added to the reaction system separately or in the form of a
complex which is prepared in advance.

[0101]The base which can be used in the present reaction is not
particularly limited and can be selected from inorganic bases such as
sodium carbonate and potassium carbonate and alkali metal alkoxides and
organic bases such as tertiary amines. Preferable examples of the base
include alkali metal alkoxides such as sodium mothoxide, sodium ethoxide,
potassium methoxide, potassium ethoxide, lithium tert-butoxide, sodium
tert-butoxide, potassium tert-butoxide and cesium carbonate
(Cs2CO3). The base may be added into the reaction field without
any treatment. Alternatively, the base may be prepared from an alkali
metal, a hydrogenated alkali metal or a alkali metal hydroxide and an
alcohol at the place of reaction and used in the reaction field.

[0102]The amount of the base is not particularly limited. It is preferable
that the amount is 0.5 mole or more per 1 mole of the halogen atom in the
two different types of aryl halides which are added to the reaction
system. When the amount of the base is less than 0.5 mol, the activity of
the reaction decreases and the yield of the arylamine decreases.
Therefore, such an amount is not preferable. When the base is added in a
great excess amount, the yield of the arylamine does not change and, on
the other hand, treatments after the reaction become complicated.
Therefore, it is more preferable that the amount is 1.0 mole or more and
less than 5 mole per 1 mole of the halogen atom.

[0103]The reaction in the process of the present invention is conducted,
in general, in the presence of an inert solvent. The solvent is not
particularly limited as long as the solvent does not adversely affect the
reaction much. Examples of the solvent include aromatic hydrocarbon
solvents such as benzene, toluene and xylene, ether solvents such as
diethyl ether, tetrahydrofuran and dioxane, acetonitrile,
dimethylformamide, dimethylsulfoxide and hexamethylphosphotriamide.
Aromatic hydrocarbon solvents such as benzene, toluene and xylene are
preferable.

[0104]It is preferable that the process of the present invention is
conducted under the ordinary pressure in an atmosphere of an inert gas
such as nitrogen and argon. The process can be conducted also under an
added pressure.

[0105]In the process of the present invention, the temperature of the
reaction can be selected in the range of 20 to 300° C. and
preferably in the range of 50 to 200° C. The time of the reaction
can be selected in the range of several minutes to 72 hours.

[0106]The process of the present invention in which the arylamine compound
is obtained in the presence of the catalyst comprising the phosphine
compound and the palladium compound and the base is specifically
described in Synthesis Examples 12, 13, 14, 17 and 20.

[0107]The present invention will be described more specifically with
reference to examples in the following. However, the present invention is
not limited to the examples.

Synthesis Example 1

Compound (2)

[0108]Synthesis of Intermediate Compound A

[0109]In a 200 ml round bottom flask, 0.38 g (2.04 mmole) of
4-bromobenzaldehyde and 0.98 g (4.29 mmole) of ethyl benzylphosphonate
were dissolved in 40 ml of dimethylsulfoxide. To this was added 0.5 g
(4.49 mmole) of potassium t-butoxide in small portions at the room
temperature and the resulting mixture was stirred for 18 hours. The
reaction mixture was poured into 500 ml of water, solid was filtered to
give yellow solid (0.5 g).

[0110]In a 100 ml round bottom flask, the crystals obtained above, 2.0 g
(12.0 mmole) of potassium iodide and 1.14 g (6.0 mmole) of copper iodide
were dissolved in 10 ml of hexamethylphosphoramide and the resulting
mixture was stirred under heating at 150° C. for 6 hours. After
the reaction was completed, 10 ml of a 1 N aqueous hydrochloric acid was
added to the reaction mixture and the organic layer was extracted with
toluene. After the extract was concentrated, the reaction product was
purified by recrystallizing from a mixture of diethyl ether and methanol
and 0.28 g (the yield: 45%) of the following Intermediate Compound A was
obtained:

##STR00067##

[0111]Synthesis of Intermediate Compound B

[0112]In a 50 ml round bottom flask, 3 g (17.4 mmole) of p-bromoaniline
was suspended in 10 ml of a 6 N aqueous hydrochloric acid and cooled. To
the cooled suspension, a solution prepared by dissolving 1.25 g (18.1
mmole) of sodium sulfite in 5.3 ml of water was slowly added dropwise at
an inner temperature of 4° C. The resulting mixture was stirred at
the same temperature for 1 hour and an aqueous solution of a diazonium
compound was obtained.

[0113]Separately, in a 100 ml round bottom flask, 0.3 g (1.7 mmole) of
anthracene was dissolved in 5 ml of acetone. To this was added a solution
prepared by dissolving 0.46 g of copper(II) chloride dihydrate in 5.7 ml
of water and the mixture was cooled to 4° C. To the cooled
mixture, the aqueous solution of a diazonium compound obtained above was
added at the same temperature and the resulting mixture was stirred for
over night at the room temperature. After the reaction was completed,
precipitated crystals were filtered, washed with methanol and dried and
0.2 g (the yield: 24%) of the following Intermediate Compound B was
obtained:

##STR00068##

[0114]Synthesis of Compound (2)

[0115]In a 100 ml round bottom flask, 0.018 g (0.2 mmole) of aniline was
dissolved in 5 ml of methylene chloride. To this was added 0.05 g (0.5
mmole) of acetic anhydride and the resulting mixture was stirred at the
room temperature for 1 hour. Then, the reaction solvent was removed by
distillation and an oily compound was obtained. To the oily compound,
0.56 g (1.8 mmole) of Intermediate Compound A, 5 g of potassium
carbonate, 0.3 g of copper powder and 20 ml of nitrobenzene were added
and the resulting mixture was stirred at 210° C. for 2 days. Then,
the solvent was removed by distillation and 10 ml of diethylene glycol
and a solution prepared by dissolving 3 g of potassium hydroxide into 10
ml of water were added. The resulting mixture was stirred at 110°
C. for one night. After the reaction was completed, a mixture of ethyl
acetate and water was added to the reaction mixture and the organic layer
was separated. After the solvent was removed by distillation, crude
crystals were obtained.

[0116]Subsequently, into a 100 ml round bottom flask, the crude crystal
obtained above, 0.05 g (0.1 mmole) of Intermediate Compound B, 5 g of
potassium carbonate, 0.3 g of copper powder and 20 ml of nitrobenzene
were placed and the mixture was stirred under heating at 220° C.
for 2 days. After the reaction was completed, precipitated crystals were
separated by filtration, washed with methanol, dried and purified in
accordance with the column chromatography (silica gel,
hexane/toluene=1/1) and 0.017 g of yellow powder was obtained. The powder
was identified to be Compound (2) by the measurements in accordance with
NMR, IR and FD-MS (the field desorption mass spectrometry) (the yield:
20%).

[0119]After the reaction was completed, the organic layer was concentrated
and about 100 g of brown crystals were obtained. The crystals were
purified in accordance with the column chromatography (silica gel,
hexane/toluene=10/1) and 28 g (the yield: 29%) of the following
Intermediate Compound C was obtained:

##STR00069##

Synthesis of Compound (9)

[0120]In a 100 ml round bottom flask, 0.48 g (1 mmole) of Intermediate
Compound B was dissolved in 10 ml of diethyl ether and the mixture was
cooled to -78° C. To the cooled mixture, 2 ml (1.5 M, 3 mmole) of
n-butyllithium was added and the resulting mixture was stirred for 1
hour. Then, a solution prepared by dissolving 0.3 g (3 mmole) of
trimethyl borate in 5 ml of diethyl ether was added dropwise to the
mixture. After the addition was completed, the resulting mixture was
stirred at -78° C. for 1 hour. Then, 10 ml of a 1 N aqueous
hydrochloric acid was added at the room temperature. After the organic
layer was separated, the solvent was removed by distillation and crude
crystals were obtained.

[0121]In a 100 ml round bottom flask, the crude crystals obtained above,
0.97 g (3 mmole) of Intermediate Compound C, 12 mg of Pd(PPh3)4
and 0.32 g (1.5 mmole) of potassium phosphate were dissolved in 10 ml of
dimethylformamide and the resulting mixture was stirred at 100° C.
for 4 hours. After the organic layer was separated, the solvent was
removed by distillation and crude crystals were obtained. The crude
crystals were purified by the column chromatography (silica gel,
benzene/ethyl acetate=50/1) to give 0.13 g of yellow powder. The powder
was identified to be Compound (9) by the measurements in accordance with
NMR, IR and FD-MS (the yield: 14%).

Synthesis Example 3

Compound (18)

[0122]Synthesis of Intermediate Compound D

[0123]A Grignard reagent was prepared by adding magnesium and diethyl
ether to 0.48 g (2.0 mmol) of 1,4-dibromobenzene. Separately, in a 100 ml
round bottom flask, 5.7 g (20.0 mmole) of 1,4-dibromonaphthalene and 10
mg of NiCl2(dppp) were dissolved in 20 ml of diethyl ether and the
resulting mixture was cooled in an ice bath. To the cooled mixture, the
Grignard reagent prepared above was added and the obtained mixture was
stirred under refluxing for 6 hours. After the reaction was completed, 10
ml of a 1 N aqueous hydrochloric acid was added. After the organic layer
was separated, the solvent was removed by distillation and 0.30 (the
yield: 30%) of the following Intermediate Compound D was obtained:

##STR00070##

[0124]Synthesis of Compound (18)

[0125]In a 100 ml round bottom flask, 0.09 g (1.0 mmole) of aniline and
0.25 g (2.5 mmole) of acetic anhydride were dissolved into 5 ml of
methylene chloride. The resulting mixture was stirred at the room
temperature for 1 hour. Then, the solvent was removed by distillation and
an oily compound was obtained. To this was added 0.4 g (4.5 mmole) of
Intermediate Compound A, 5 g of potassium carbonate, 0.3 g of copper
powder and 20 ml of nitrobenzene and the resulting mixture was stirred
under heating at 210° C. for 2 days. Then, the solvent was removed
by distillation and 10 ml of diethylene glycol and a solution prepared by
dissolving 3 g of potassium hydroxide into 10 ml of water were added to
the residue. The resulting mixture was stirred at 110° C. for one
night. After the reaction was completed, a mixture of ethyl acetate and
water was added to the reaction mixture. After the organic layer was
separated, the solvent was removed and crude crystals were obtained.

[0126]Subsequently, into a 100 ml round bottom flask, the above crude
crystals, 0.5 g (1.0 mmole) of Intermediate Compound D, 5 g of potassium
carbonate and 0.3 g of copper powder were dissolved in 20 ml of
nitrobenzene and the resulting mixture was stirred under heating at
220° C. for 2 days. After the reaction was completed, precipitated
crystals were filtered, washed with methanol, dried and purified by the
column chromatography (silica gel, hexane/toluene=1/1) to give 0.1 g of
yellow powder. The powder was identified to be Compound (18) by the
measurements in accordance with NMR, IR and FD-MS (the yield: 10%).

Example 1

[0127]A cleaned glass plate having an ITO electrode was coated with a
composition which contained Compound (2) obtained above as the light
emitting material, 2,5-bis(1-naphthyl)-1,3,4-oxadiazole and a
polycarbonate resin (manufactured by TEIJIN KASEI Co., Ltd.; PANLITE
K-1300) in amounts such that the ratio by weight was 5:3:2 and was
dissolved in tetrahydrofuran in accordance with the spin coating and a
light emitting layer having a thickness of 100 nm was obtained. On the
obtained light emitting layer, an electrode having a thickness of 150 nm
was formed with an alloy prepared by mixing aluminum and lithium in
amounts such that the content of lithium was 3% by weight and an organic
EL device was obtained. The organic EL device exhibited a luminance of
emitted light of 200 (cd/m2), the maximum luminance of 14,000
(cd/m2) and an efficiency of light emission of 2.1 (lm/W) under
application of a direct current voltage of 5 V.

Example 2

[0128]On a cleaned glass plate having an ITO electrode, Compound (9)
obtained above was vacuum vapor deposited as the light emitting material
and a light emitting layer having a thickness of 100 nm was formed. On
the layer formed above, an electrode having a thickness of 100 nm was
formed with an alloy prepared by mixing aluminum and lithium in amounts
such that the content of lithium was 3% by weight and an organic EL
device was obtained. The light emitting layer was formed by vapor
deposition under a vacuum of 10-6 Torr while the temperature of the
substrate was kept at the room temperature. The organic EL device
exhibited a luminance of emitted light of about 110 (cd/m2), the
maximum luminance of 20,000 (cd/m2) and an efficiency of light
emission of 2.1 (lm/W) under application of a direct current voltage of 5
V.

Example 3

[0129]On a cleaned glass plate having an ITO electrode, Compound (2)
obtained above was vacuum vapor deposited as the light emitting material
and a light emitting layer having a thickness of 50 nm was formed. Then,
an electron injecting layer having a thickness of 10 nm was formed by
vapor deposition of the following compound (Alq):

##STR00071##

On the layer formed above, an electrode having a thickness of 100 nm was
formed with an alloy prepared by mixing aluminum and lithium in amounts
such that the content of lithium was 3% by weight and an organic EL
device was obtained. The light emitting layer and the electron injecting
layer were formed by vapor deposition under a vacuum of 10-6 Torr
while the temperature of the substrate was kept at the room temperature.
The organic EL device emitted bluish green light with a luminance of
emitted light of about 600 (cd/m2), the maximum luminance of 30,000
(cd/m2) and an efficiency of light emission of 3.0 (lm/W) under
application of a direct current voltage of 5 V. When the organic EL
device was driven by a constant electric current at an initial luminance
of emitted light of 600 (cd/m2), the half life time was as long as
2,000 hours.

Examples 4 to 16

[0130]On a cleaned glass plate having an ITO electrode, the light emitting
material shown in Table 1 was vapor deposited and a light emitting layer
having a thickness of 80 nm was obtained. Then, the compound (Alq)
described above was vacuum vapor deposited as the electron injecting
material and an electron injecting layer having a thickness of 20 nm was
formed. On the layer formed above, an electrode having a thickness of 150
nm was formed with an alloy prepared by mixing aluminum and lithium in
amounts such that the content of lithium was 3% by weight. Organic EL
devices were obtained in this manner. The above layers were formed by
vapor deposition under a vacuum of 10-6 Torr while the temperature
of the substrate was kept at the room temperature. The light emitting
properties of the obtained devices are shown in Table 1. The organic EL
devices in these Examples all showed excellent luminances such as the
maximum luminance of 10,000 (cd/m2) or greater.

[0131]On a cleaned glass plate having an ITO electrode, the following
compound (TPD74):

##STR00072##

was vacuum vapor deposited as the hole injecting material and a film
having a thickness of 60 nm was formed. Then, the following compound
(NPD):

##STR00073##

was vacuum vapor deposited on the film formed above as the hole
transporting material and a film having a thickness of 20 nm was formed.
Then, 4,4'-bis(2,2-diphenylvinyl)biphenyl (DPVBi) and Compound (3)
obtained above were vapor deposited simultaneously and a layer having a
content of Compound (3) of 5% by weight and the thickness of 40 nm was
formed. Compound (3) works as the fluorescent dopant. Subsequently, the
compound (Alq) was vapor deposited as the electron injecting material and
a layer having a thickness of 20 nm was formed. Then, LiF was vapor
deposited and a layer having a thickness of 0.5 nm was formed. An
electrode was formed on the above layers by vapor deposition of aluminum
and a layer having a thickness of 100 nm was formed. Thus, an organic EL
was obtained. The above layers were formed by vapor deposition under a
vacuum of 10-6 Torr while the temperature of the substrate was kept
at the room temperature. The organic EL device exhibited a luminance of
emitted light as high as about 750 (cd/m2) under application of a
direct current voltage of 5 V. When the organic EL device was driven by a
constant electric current at an initial luminance of emitted light of 400
(cd/m2), the half life time was as long as 3,000 hours.

Comparative Example 1

[0132]An organic EL device was prepared in accordance with the same
procedures as those conducted in Example 1 except that the following
Compound of Comparative Example 1:

##STR00074##

[0133](Compound of Comparative Example 1)

was used as the light emitting material. The obtained organic EL device
exhibited a luminance of emitted light of 60 (cd/m2) and an
efficiency of light emission of 0.34 (lm/W) under application of a direct
current voltage of 5 V. Sufficient properties could not be obtained.

Comparative Example 2

[0134]An organic EL device was prepared in accordance with the same
procedures as those conducted in Example 3 except that the following
Compound of Comparative Example 2:

##STR00075##

[0135](Compound of Comparative Example 2)

was used as the light emitting material. The obtained organic EL device
exhibited a luminance of emitted light of 200 (cd/m2) and an
efficiency of light emission of 1.2 (lm/W) under application of a direct
current voltage of 5 V. However, when the organic EL device was driven by
a constant electric current at an initial luminance of emitted light of
400 (cd/m2), the half life time was as short as 600 hours.

Test of Heat Resistance

[0136]The organic EL devices prepared in Examples 2 and 3 and Comparative
Examples 1 and 2, which had been used for the measurement of luminance of
emitted light, were placed in a chamber kept at the constant temperature
of 100° C. After 500 hours, luminance of light emission was
measured again. The values of luminance before and after the devices were
kept in the chamber were compared and the retention of luminance was
calculated.

[0137]The retentions of luminance of the organic EL devices prepared in
Examples 2 and 3 and Comparative Examples 1 and 2 thus obtained were 85%,
90%, 25% and 30%, respectively. As shown by this result, the compounds
used as the light emitting material in Comparative Examples 1 and 2 could
not retain luminance because the compounds had glass transition
temperatures lower than 100° C. In contrast, the compounds used as
the light emitting material in Examples 2 and 3 exhibited excellent heat
resistance and could retain luminance for a long time because the
compounds had glass transition temperatures higher than 110° C.

Synthesis Example 4

Compound (30)

Synthesis of Intermediate Compound E (6,12-diiodochrysene)

[0138]In a 300 ml round bottom flask, 5 g (22 mmole) of chrysene was
dissolved in 100 ml of carbon tetrachloride. To this was added 16 g (64
mmole) of iodine dissolved in 100 ml of carbon tetrachloride dropwise at
the room temperature. The resulting mixture was stirred under heating for
5 hours, precipitated crystals were separated by filtration and the
crystals were washed with 100 ml of carbon tetrachloride. The crude
crystals were recrystallized from 200 ml of toluene and Intermediate
Compound E was obtained (the yield: 35%).

[0139]Synthesis of Compound (30)

[0140]In a 100 ml two-necked flask, 2 g (10 mmole) of 4-aminostilbene was
dissolved in 20 ml of methylene chloride. To this was added 2.5 g (25
mmole) of acetic anhydride. The resulting mixture was stirred at the room
temperature for 1 hour. Then, the reaction solvent was removed by
distillation and an oily compound was obtained. In a 300 ml two-necked
flask, 4.1 g (20 mmole) of iodobenzene, 3 g (30 mmole) of potassium
carbonate, 0.06 g (1 mmole) of copper powder and 100 ml of nitrobenzene
were added to the obtained oily compound and the obtained mixture was
stirred under heating at 220° C. for 2 days. Then, the solvent was
removed by distillation and 10 ml of diethylene glycol and a solution
prepared by dissolving 30 g of potassium hydroxide into 100 ml of water
were added to the residue. The reaction was allowed to proceed at
110° C. for one night. After the reaction was completed, a mixture
of ethyl acetate and water was added to the reaction mixture. After the
organic layer was separated, the solvent was removed by distillation and
crude crystals were obtained.

[0141]Subsequently, in a 300 ml two-necked flask, the above crude
crystals, 2.4 g (5 mmole) of Intermediate Compound E, 3 g (20 mmole) of
potassium carbonate and 0.06 g (1 mmole) of copper powder were dissolved
in 100 ml of nitrobenzene and the resulting mixture was stirred under
heating at 230° C. for 2 days. After the reaction was completed,
precipitated crystals were separated by filtration, washed with methanol,
dried and purified in accordance with the column chromatography (silica
gel, hexane/toluene=1/1) and 1.0 g of yellow powder was obtained. The
powder was identified to be Compound (30) by the measurements in
accordance with NMR, IR and FD-MS (the yield: 25%).

Synthesis Example 5

Compound (36)

[0142]Synthesis of Compound (36)

[0143]In a 100 ml round bottom flask, 3.4 g (20 mmole) of diphenylamine,
4.8 g (10 mmole) of Intermediate Compound E, 3 g (30 mmole) of potassium
carbonate and 0.06 g (1 mmole) of copper powder were dissolved in 100 ml
of nitrobenzene and the resulting mixture was stirred under heating at
210° C. for 2 days. After the reaction was completed, precipitated
crystals were separated by filtration, washed with methanol, dried and
purified in accordance with the column chromatography (silica gel,
hexane/toluene=1/1) and 2.8 g of yellow powder was obtained. The powder
was identified to be Compound (36) by the measurements in accordance with
NMR, IR and FD-MS (the yield: 50%).

Synthesis Example 6

Compound (38)

[0144]Synthesis of Compound (38)

[0145]In a 100 ml four-necked flask, 1.0 g (41 mmole) of magnesium, 1 ml
of tetrahydrofuran and a small piece of iodine were placed under an argon
stream. To this mixture, 9.7 g (30 mmole) of 4-bromotriphenylamine
dissolved in 100 ml of tetrahydrofuran was slowly added dropwise at the
room temperature. After the addition was completed, the reaction mixture
was stirred under heating at 60° C. for 1 hour and a Grignard
reagent was prepared.

[0146]In a 300 ml four-necked flask, 4.8 g (10 mmole) of Intermediate
Compound E, 0.28 g (0.4 mmole) of PdCl2(PPh3)2 and 1.0 ml
(1 mmole) of a 1.0 M toluene solution of AlH(iso-Bu)2 were dissolved
in 50 ml of tetrahydrofuran under an argon stream. To this was added the
Grignard reagent prepared above dropwise at the room temperature. The
temperature was elevated and the reaction mixture was heated under
refluxing for over night. After the reaction was completed, the reaction
liquid was cooled with ice water. Precipitated crystals were separated by
filtration and washed with acetone. The obtained crude crystals were
recrystallized from 100 ml of acetone and 4.3 g of yellow powder was
obtained. The powder was identified to be Compound (38) by the
measurement in accordance with NMR, IR and FD-MS (the yield: 60%).

Synthesis Example 7

Compound (47)

[0147]Synthesis of Compound (47)

[0148]In a 100 ml two-necked flask, 2.4 g (10 mmole) of 6-aminochrysene
was dissolved into 20 ml of methylene chloride. To this was added 2.5 g
(25 mmole) of acetic anhydride and the resulting mixture was stirred at
the room temperature for 1 hour. Then, the reaction solvent was removed
by distillation and an oily compound was obtained. In a 300 ml two-necked
flask, 4.1 g (20 mmole) of iodobenzene, 3 g (30 mmole) of potassium
carbonate and 0.06 g (1 mmole) of copper powder were dissolved in 100 ml
of nitrobenzene. To this was added the oily compound and the resulting
mixture was stirred under heating at 220° C. for 2 days. Then, the
solvent was removed by distillation and 10 ml of diethylene glycol and a
solution prepared by dissolving 30 g of potassium hydroxide into 100 ml
of water were added to the residue. The reaction was allowed to proceed
at 110° C. for one night. After the reaction was completed, a
mixture of ethyl acetate and water was added to the reaction mixture.
After the organic layer was separated, the solvent was removed by
distillation and crude crystals were obtained.

[0149]Subsequently, in a 300 ml two-necked flask, the crude crystals
obtained above, 2 g (5 mmole) of 4,4'-diiodobiphenyl, 3 g (30 mmole) of
potassium carbonate and 0.06 g (1 mmole) of copper powder were dissolved
in 100 ml of nitrobenzene and the resulting mixture was stirred under
heating at 230° C. for 2 days. After the reaction was completed,
precipitated crystals were separated by filtration, washed with methanol,
dried and purified in accordance with the column chromatography (silica
gel, hexane/toluene=1/3) and 0.8 g of yellow powder was obtained. The
powder was identified to be Compound (47) by the measurements in
accordance with NMR, IR and FD-MS (the yield: 30%).

Example 18

[0150]A cleaned glass plate having an ITO electrode was coated with a
composition which contained Compound (30) obtained above as the light
emitting material, 2,5-bis(1-naphthyl)-1,3,4-oxadiazole and a
polycarbonate resin (manufactured by TEIJIN KASEI Co., Ltd.; PANLITE
K-1300) in amounts such that the ratio by weight was 5:3:2 and was
dissolved in tetrahydrofuran in accordance with the spin coating and a
light emitting layer having a thickness of 100 nm was obtained. On the
obtained light emitting layer, an electrode having a thickness of 150 nm
was formed with an alloy prepared by mixing aluminum and lithium in
amounts such that the content of lithium was 3% by weight and an organic
EL device was obtained. The organic EL device exhibited a luminance of
emitted light of 320 (cd/m2), the maximum luminance of 14,000
(cd/m2) and an efficiency of light emission of 2.5 (lm/W) under
application of a direct current voltage of 5 V.

Example 19

[0151]On a cleaned glass plate having an ITO electrode, Compound (37)
obtained above was vacuum vapor deposited as the light emitting material
and a light emitting layer having a thickness of 100 nm was formed. On
the layer formed above, an inorganic electron injecting layer having a
thickness of the film of 0.3 nm was formed with lithium fluoride. Then,
an electrode having a thickness of 100 nm was formed with aluminum and an
organic EL device was obtained. The light emitting layer was formed by
vapor deposition under a vacuum of 10-6 Torr while the temperature
of the substrate was kept at the room temperature. The organic EL device
exhibited a luminance of emitted light of about 110 (cd/m2), the
maximum luminance of 20,000 (cd/m2) and an efficiency of light
emission of 1.2 (lm/W) under application of a direct current voltage of 5
V.

Example 20

[0152]On a cleaned glass plate having an ITO electrode, CuPc was vacuum
vapor deposited as the hole injecting material and a hole injecting layer
having a thickness of 40 nm was formed. Then, a hole transporting layer
having a thickness of 20 nm was formed by using Compound (47) obtained
above as the hole transporting material and a light emitting layer having
a thickness of 60 nm was formed by vacuum vapor deposition of the
compound (Alq) described above. Rubrene was added to the light emitting
layer in an amount of 4% by weight. On the layers formed above, an
electrode having a thickness of 100 nm was formed with an alloy prepared
by mixing aluminum and lithium in amounts such that the content of
lithium was 3% by weight and an organic EL device was obtained. The above
layers were formed by vapor deposition under a vacuum of 10-6 Torr
while the temperature of the substrate was kept at the room temperature.
The organic EL emitted green light with a luminance of emitted light of
about 700 (cd/m2), the maximum luminance of 80,000 (cd/m2) and
an efficiency of light emission of 6.0 (lm/W) under application of a
direct current voltage of 5 V. When the organic EL device was driven by a
constant electric current at an initial luminance of emitted light of 600
(cd/m2), the half life time was as long as 4,000 hours.

Examples 21 to 33

[0153]On a cleaned glass plate having an ITO electrode, a hole injecting
layer having a thickness of 20 nm was formed by vacuum vapor deposition
of the hole injecting material shown in Table 2. A light emitting layer
having a thickness of 60 nm was formed by vapor deposition of the
compound (Alq) described above as the light emitting material and rubrene
was added to the light emitting layer in an amount of 4% by weight. On
the layers formed above, an electrode having a thickness of 150 nm was
formed with an alloy prepared by mixing aluminum and lithium in amounts
such that the content of lithium was 3% by weight. Organic EL devices
were obtained in this manner. The above layers were formed by vapor
deposition under a vacuum of 10-6 Torr while the temperature of the
substrate was kept at the room temperature. The light emitting properties
of the obtained devices are shown in Table 2. The organic EL devices in
these Examples all showed excellent luminances such as the maximum
luminance of 10,000 (cd/m2) or greater.

[0154]On a cleaned glass plate having an ITO electrode, compound (TPD74)
described above was vacuum vapor deposited as the hole injecting material
and a layer having a thickness of 60 nm was formed. Then, the compound
(NPD) obtained above was vacuum vapor deposited as the hole transporting
material and a layer having a thickness of 20 nm was formed.

[0155]4,4'-bis(2,2-Diphenylvinyl)phenylanthracene (DPVDPAN) as the light
emitting material and Compound (36) described above as the dopant were
vapor deposited simultaneously and a layer which had a content of
Compound (36) of 2% by weight and a thickness of 40 nm was formed. Then,
the compound (Alq) described above was vapor deposited as the charge
injecting material and a layer having a thickness of 20 nm was formed.
After lithium fluoride was vapor deposited and a layer having a thickness
of 0.5 nm was formed, aluminum was vapor deposited and an electrode
having a thickness was 100 nm formed. Thus, an organic EL device was
obtained. The above layers were formed by vapor deposition under a vacuum
of 10-6 Torr while the temperature of the substrate was kept at the
room temperature. The organic EL device exhibited a luminance of emitted
light as high as 500 (cd/m2) under application of a direct current
voltage of 8 V and the emitted light had blue color of excellent purity.
When the organic EL device was driven by a constant electric current at
an initial luminance of emitted light of 100 (cd/m2), the half life
time was as long as 7,000 hours.

[0156]The spectrum of the light emitted by this device was measured and it
was found that the spectrum was the same as that of the device using
DPVBi. This means that Compound (36) did not affect the light emission
but exhibited the effect of extending the life of the device.

Comparative Example 3

[0157]An organic EL device was prepared in accordance with the same
procedures as those conducted in Example 34 except that Compound (36)
described above was not added as the dopant. When the prepared organic EL
device was driven by a constant electric current at an initial luminance
of emitted light of 100 (cd/m2), the half life time was shorter than
the half life time in Example 34, i.e., 4,000 hours.

Comparative Example 4

[0158]An organic EL device was prepared in accordance with the same
procedures as those conducted in Example 20 except that Compound of
Comparative Example 2 described above was used as the hole transporting
material.

[0159]The prepared organic EL device exhibited a luminance of emitted
light of 300 (cd/m2) and an efficiency of light emission of 4.2
(lm/W) under application of a direct current voltage of 5 V. However,
when the organic EL device was driven by a constant electric current at
an initial luminance of emitted light of 400 (cd/m2), the half life
time was as short as 300 hours.

Test of Heat Resistance

[0160]The organic EL devices prepared in Examples 20 and 27 and
Comparative Example 4, which had been used for the measurement of
luminance of emitted light, were placed in a chamber kept at the constant
temperature of 105° C. After 500 hours, luminance of light
emission was measured again. The values of luminance before and after the
devices were kept in the chamber were compared and the retention of
luminance was calculated.

[0161]The retentions of luminance of the organic EL devices prepared in
Examples 20 and 27 and Comparative Example 4 thus obtained were 87%, 90%
and 25%, respectively. As shown by this result, the compounds used as the
light emitting material in Comparative Example 4 could not retain
luminance because the compounds had a glass transition temperature lower
than 105° C. In contrast, the compounds used for the light
emitting material in Examples 20 and 27 exhibited excellent heat
resistance and could retain luminance for a long time because the
compounds had glass transition temperatures higher than 110° C.

Synthesis Example 8

Compound (58)

Synthesis of Intermediate Compound F (5,11-dibromonaphthacene)

[0162]In a 2 liter round bottom flask, 50 g (0.19 mmole) of
5,12-naphthacene, 108 g (0.57 mmole) of tin(IV) chloride, 500 ml of
acetic acid and 200 ml of concentrated hydrochloric acid were placed. The
resulting mixture was stirred for reflux for 2 hours. After the reaction
was completed, precipitated crystals were separated by filtration, washed
with water and dried in a vacuum drying chamber and 48 g of crude
crystals were obtained.

[0163]Subsequently, in a 2 liter four-necked flask, the crude crystals
obtained above and 50 g (0.19 mmole) of triphenylphosphine were dissolved
in 300 ml of dimethylformamide under an argon stream. To this was added
64 g (0.4 mmole) of bromine dissolved in 200 ml of dimethylformamide
slowly dropwise and the resulting mixture was stirred at ambient
temperature. After the addition was completed, the mixture was stirred
under heating at 200° C. for one night. After the reaction was
completed, dimethylformamide was removed by distillation in vacuo and 200
ml of water was added to the residue. The organic layer was extracted
with toluene. The extract was dried with magnesium sulfate and
concentrated in vacuo using a rotary evaporator and an oily compound was
obtained. The oily compound was purified in accordance with the column
chromatography (silica gel, hexane/toluene=1/1) and 30 g of yellow powder
was obtained. The powder was identified to be Intermediate Compound F by
the measurements in accordance with NMR, IR and FD-MS (the yield: 40%).

[0164]Synthesis of Compound (58)

[0165]In a 100 ml two-necked flask, 2 g (10 mmole) of 4-aminostilbene was
dissolved in 20 ml of methylene chloride. To this was added 2.5 g (25
mmole) of acetic anhydride and the resulting mixture was stirred at the
room temperature for 1 hour. Then, the reaction solvent was removed by
distillation and an oily compound was obtained. In a 300 ml two-necked
flask, 4.1 g (20 mmole) of iodobenzene, 3 g (30 mmole) of potassium
carbonate, 0.06 g (1 mmole) of copper powder and 100 ml of nitrobenzene
were added to the obtained oily compound and the obtained mixture was
stirred under heating at 220° C. for 2 days. Then, the solvent was
removed by distillation and 10 ml of diethylene glycol and a solution
prepared by dissolving 30 g of potassium hydroxide into 100 ml of water
were added to the residue. The reaction was allowed to proceed at
110° C. for one night. After the reaction was completed, a mixture
of ethyl acetate and water was added to the reaction mixture. After the
organic layer was separated, the solvent was removed and crude crystals
were obtained.

[0166]Subsequently, in a 100 ml two-necked flask, the crude crystals
obtained above, 1.9 g (5 mmole) of Intermediate Compound F, 1.3 g (12
mmole) of potassium t-butoxide and 40 mg (5% by mole) of
PdCl2(PPh3)2 were dissolved in 30 ml of xylene under an
argon stream. The resulting mixture was stirred under heating at
130° C. for over night. After the reaction was completed,
precipitated crystals were separated by filtration, washed with methanol,
dried and purified in accordance with the column chromatography (silica
gel, hexane/toluene=1/1) and 0.9 g of yellow powder was obtained. The
powder was identified to be Compound (58) by the measurements in
accordance with NMR, IR and FD-MS (the yield: 25%).

Synthesis Example 9

Synthesis of Compound (59)

[0167]In a 300 ml four-necked flask, 2 g (10 mmole) of 4-hydroxystilbene
and 5.2 g (20 mmole) of triphenylphosphine were dissolved in 50 ml of
dimethylformamide under an argon stream. To this mixture was added 5 g
(20 mmole) of iodine dissolved in 50 ml of dimethylformamide slowly
dropwise at the room temperature and the reaction was allowed to proceed.
After the addition was completed, the reaction mixture was stirred at
200° C. for over night. After the reaction was completed,
dimethylformamide was removed by distillation in vacuo and 200 ml of
water was added to the residue. The organic layer was extracted with
toluene. The extract was dried with magnesium sulfate and concentrated in
vacuo using a rotary evaporator and an oily compound was obtained. The
oily compound was purified in accordance with the column chromatography
(silica gel, hexane/toluene=1/1) and 2.5 g of yellow powder was obtained.

[0168]Separately, in a 100 ml two-necked flask, 2 g (10 mmole) of
4-aminostilbene was dissolved in 20 ml of methylene chloride. To this was
added 2.5 g (25 mmole) of acetic anhydride and the resulting mixture was
stirred at the room temperature for 1 hour. Then, the reaction solvent
was removed by distillation and an oily compound was obtained.

[0169]In a 300 ml two-necked flask, 2.5 g of the yellow powder obtained
above, 3 g (30 mmole) of potassium carbonate, 0.06 g (1 mmole) of copper
powder and 100 ml of nitrobenzene were added to the above oily compound.
The resulting mixture was stirred under heating at 220° C. for 2
days. To the residue obtained by removing the solvent from the above
mixture by distillation, 10 ml of diethylene glycol and 30 g of potassium
hydroxide dissolved in 100 ml of water were added and the reaction was
allowed to proceed at 110° C. for over night. After the reaction
was completed, a mixture of ethyl acetate and water was added to the
reaction mixture. After the organic layer was separated, the solvent was
removed by distillation and crude crystals were obtained.

[0170]Subsequently, in a 300 ml two-necked flask, the above crude
crystals, 2.4 g (5 mmole) of Intermediate Compound F, 1.3 g (12 mmole) of
potassium t-butoxide and 40 mg (5% by mole) of
PdCl2(PPh3)2 were dissolved in 30 ml of xylene under an
argon stream. The resulting mixture was stirred under heating at
130° C. and the reaction was allowed to proceed for over night.
After the reaction was completed, precipitated crystals were separated by
filtration, washed with methanol, dried and purified by the column
chromatography (silica gel, hexaneltoluene=1/1) and 0.2 g of yellow
powder was obtained. The powder was identified to be Compound (59) by the
measurements in accordance with NMR, IR and FD-MS (the yield: 5%).

Synthesis Example 10

Compound (61)

[0171]Synthesis of Compound (61)

[0172]In a 300 ml four-necked flask, 9.7 g (30 mmole) of
4-bromotriphenylamine, 50 ml of toluene and 50 ml of diethyl ether were
placed and the resulting mixture was cooled with ice water under an argon
stream. To the cooled mixture, a mixture of 22 ml (33 mmole) of a hexane
solution (1.52 mole/liter) of n-butyllithium and 100 ml of
tetrahydrofuran were slowly added dropwise at the room temperature and
the resulting mixture was stirred. After 4.3 g (10 mmole) of
6,13-dibromopenthacene was added to the reaction mixture, the obtained
mixture was stirred at the same temperature for one night. After the
reaction was completed, 500 ml of water was added to the reaction mixture
and the organic layer was extracted with diethyl ether. The extract was
dried with magnesium sulfate and concentrated in vacuo using a rotary
evaporator and 7.4 g of an oily compound was obtained.

[0173]In a 300 ml four-necked flask, the above compound, 6.6 g (40 mmole)
of potassium iodide and 100 ml of acetic acid were placed and the
resulting mixture was heated under refluxing for 1 hour. After the
reaction was completed, the reaction mixture was cooled to the room
temperature and precipitated crystals were separated by filtration. The
obtained crystals were washed with water and acetone and 2.7 g of orange
solid was obtained. The orange solid was identified to be Compound (61)
by the measurement in accordance with NMR, IR and FD-MS (the yield: 35%).

Synthesis Example 11

Compound (62)

Synthesis of Intermediate Compound G (5,11-diiodonaphthacene)

[0174]In a 500 ml round bottom flask, 50 g (0.22 mmole) of naphthacene and
200 ml of tetrachloroethane were placed. To this was added 160 g (0.64
mole) of iodine dissolved in 200 ml of carbon tetrachloride slowly
dropwise at the room temperature and the resulting mixture was stirred
under heating for 5 hours. Precipitated crystals were separated by
filtration and washed with 500 ml of methanol. The obtained crude
crystals were recrystallized from 200 ml of toluene and 34 g of
Intermediate Compound G was obtained (the yield: 40%).

[0175]Synthesis of Compound (62)

[0176]In a 100 ml four-necked flask, 1.0 g (41 mmole) of magnesium, 1 ml
of tetrahydrofuran and a small piece of iodine were placed under an argon
stream. To this was added 9.7 g (30 mmole) of 4-bromotriphenylamine
dissolved in 100 ml of tetrahydrofuran slowly dropwise at the room
temperature. After the addition was completed, the resulting mixture was
stirred under heating at 60° C. for 1 hour and a Grignard reagent
was prepared.

[0177]In a 300 ml four-necked flask, 4.8 g (10 mmole) of Intermediate
Compound G, 0.28 g (0.4 mmole) of PdCl2(PPh3)2 and 1.0 ml
(1 mmole) of a 1.0 M toluene solution of AlH(iso-Bu)2 were dissolved
in 50 ml of tetrahydrofuran under an argon stream. To the this mixture,
the Grignard reagent prepared above was added dropwise at the room
temperature. The temperature was elevated and the reaction mixture was
heated under refluxing for one night. After the reaction was completed,
the reaction liquid was cooled with ice water. Precipitated crystals were
separated by filtration and washed with acetone. The obtained crude
crystals were recrystallized from 100 ml of acetone and 3.6 g of yellow
powder was obtained. The powder was identified to be Compound (62) by the
measurement in accordance with NMR, IR and FD-MS (the yield: 50%).

Example 35

[0178]A cleaned glass plate having an ITO electrode was coated with a
composition which contained Compound (58) obtained above as the light
emitting material, 2,5-bis(1-naphthyl)-1,3,4-oxadiazole and a
polycarbonate resin (manufactured by TEIJIN KASEI Co., Ltd.; PANLITE
K-1300) in amounts such that the ratio by weight was 5:2:2 and was
dissolved in tetrahydrofuran in accordance with the spin coating and a
light emitting layer having a thickness of 100 nm was obtained. On the
obtained light emitting layer, an electrode having a thickness of 150 nm
was formed with an alloy prepared by mixing aluminum and lithium in
amounts such that the content of lithium was 3% by weight and an organic
EL device was obtained. The organic EL device emitted yellowish orange
light with a luminance of emitted light of 130 (cd/m2), the maximum
luminance of 14,000 (cd/m2) and an efficiency of light emission of
1.2 (lm/W) under application of a direct current voltage of 5 V.

Example 36

[0179]On a cleaned glass plate having an ITO electrode, Compound (71)
obtained above was vacuum vapor deposited as the light emitting material
and a light emitting layer having a thickness of 100 nm was prepared. On
the obtained light emitting layer, an electrode having a thickness of 100
nm was formed with an alloy prepared by mixing aluminum and lithium in
amounts such that the content of lithium was 3% by weight and an organic
EL device was obtained. The light emitting layer was formed by vapor
deposition under a vacuum of 10-6 Torr while the temperature of the
substrate was kept at the room temperature. The organic EL device emitted
orange light with a luminance of emitted light of 120 (cd/m2), the
maximum luminance of 1,800 (cd/m2) and an efficiency of light
emission of 0.3 (lm/W) under application of a direct current voltage of 5
V.

Example 37

[0180]On a cleaned glass plate having an ITO electrode, Compound (71)
obtained above was vacuum vapor deposited as the light emitting material
and a light emitting layer having a thickness of 50 nm was prepared.
Then, the compound (Alq) described above was vacuum vapor deposited on
the obtained light emitting layer and an electron injection layer having
a thickness of 10 nm was formed. On the formed layer, an electrode having
a thickness of 100 nm was formed with an alloy prepared by mixing
aluminum and lithium in amounts such that the content of lithium was 3%
by weight and an organic EL device was obtained. The light emitting layer
and the electron injecting layer were formed by vapor deposition under a
vacuum of 10-6 Torr while the temperature of the substrate was kept
at the room temperature. The organic EL device emitted orange light with
a luminance of emitted light of about 200 (cd/m2), the maximum
luminance of 12,000 (cd/m2) and an efficiency of light emission of
1.0 (lm/W) under application of a direct current voltage of 5 V.

Examples 38 to 46

[0181]On a cleaned glass plate having an ITO electrode, a light emitting
material shown in Table 3 was vacuum vapor deposited and a light emitting
layer having a thickness of 80 nm was prepared. Then, the compound (Alq)
described above was vacuum vapor deposited on the obtained light emitting
layer and an electron injecting layer having a thickness of 20 nm was
formed. On the formed layer, an electrode having a thickness of 150 nm
was formed with an alloy prepared by mixing aluminum and lithium in
amounts such that the content of lithium was 3% by weight. In this
manner, organic EL devices were obtained. The above layers were formed by
vapor deposition under a vacuum of 10-6 Torr while the temperature
of the substrate was kept at the room temperature. The properties of
light emission of the obtained organic EL devices are shown in Table 3.
The organic EL devices in these Examples all showed excellent luminances
such as the maximum luminance of 5,000 (cd/m2) or greater.

[0182]On a cleaned glass plate having an ITO electrode, the compound
(TPD74) described above was vacuum vapor deposited as the hole injecting
material and a layer having a thickness of 60 nm was formed. Then, the
compound (NPD) described later was vapor deposited as the hole
transporting material and a layer having a thickness of 20 nm was formed.

[0183]Then, 4,4'-bis(2,2-diphenylvinyl)biphenyl (DPVBi) and Compound (58)
described above were simultaneously vacuum deposited as the light
emitting materials and a layer having a content of Compound (58) of 5% by
weight and a thickness of 40 nm was formed. Compound (58) worked also as
a fluorescent dopant. Then, the compound (Alq) described above was vapor
deposited as the election injection material and a layer having a
thickness of 20 nm was formed. On the formed layer, lithium fluoride was
vapor deposited and a layer having a thickness of 0.5 nm was formed.
Then, aluminum was vapor deposited and a layer having a thickness of 100
nm was formed. Thus, an electrode was formed and an organic EL device was
obtained. The above layers were formed by vapor deposition under a vacuum
of 10-6 Torr while the temperature of the substrate was kept at the
room temperature. The organic EL device emitted yellow light with a
luminance of emitted light of about 600 (cd/m2) under application of
a direct current voltage of 5 V. When the organic EL device was driven by
a constant electric current at an initial luminance of emitted light of
400 (cd/m2), the half life time was as long as 2,800 hours.

Example 48

[0184]An organic EL device was prepared in accordance with the same
procedures as those conducted in Example 47 except that the light
emitting layer was formed by simultaneously vapor depositing the compound
(Alq) described above as the light emitting material and Compound (61)
described above as the dopant and a light emitting layer having the
content of Compound (61) of 5% by weight was formed. The organic EL
device emitted red light with a luminance of emitted light of about 240
(cd/m2) under application of a direct current voltage of 5 V. When
the organic EL device was driven by a constant electric current at an
initial luminance of emitted light of 400 (cd/m2), the half life
time was as long as 3,200 hours.

Comparative Example 5

[0185]An organic EL device was prepared in accordance with the same
procedures as those conducted in Example 35 except that (Compound of
Comparative Example 1) described above was used as the light emitting
material.

[0186]The organic EL device exhibited luminance of emitted light of about
60 (cd/m2) and an efficiency of light emission of 0.34 (lm/W) under
application of a direct current voltage of 5V. Sufficient properties
could not be obtained. The emitted light was blue light.

Comparative Example 6

[0187]An organic EL device was prepared in accordance with the same
procedures as those conducted in Example 37 except that (Compound of
Comparative Example 2) described above was used as the light emitting
material.

[0188]The organic EL device exhibited a luminance of emitted light of
about 200 (cd/m2) and an efficiency of light emission of 1.2 (lm/W)
under application of a direct current voltage of 5 V. However, when the
organic EL device was driven by a constant electric current at an initial
luminance of emitted light of 400 (cd/m2), the half life time was as
short as 600 hours. The emitted light was blue light.

Comparative Example 7

[0189]An organic EL device was prepared in accordance with the same
procedures as those conducted in Example 47 except that (Compound of
Comparative Example 1) described above was used in place of Compound
(58).

[0190]The organic EL device exhibited a luminance of emitted light of
about 200 (cd/m2) under application of a direct current voltage of 5
V. However, when the organic EL device was driven by a constant electric
current at an initial luminance of emitted light of 400 (cd/m2), the
half life time was as short as 700 hours. The emitted light was blue
light.

Synthesis Example 12

Compound (75)

[0191]Synthesis of Compound (75)

[0192]In a 200 ml three-necked flask, 2.16 g (5.5 mmole) of
6,12-dibromonaphthacene (40577-78-4), 0.06 g (0.3 mmole) of
Pd(OAc)2, 0.23 g (1.1 mmole) of P(tBu)3, 1.51 g (15.7 mmole) of
NaOtBu and 1.89 g (11.2 mmole) of Ph2NH were dissolved in 25 ml of
toluene under an argon stream. The resulting mixture was stirred under
heating at 120° C. and the reaction was allowed to proceed for 7
hours. After the reaction was completed, the reaction mixture was left
standing and cooled. After red crystals were separated by filtration, the
crystals were washed with toluene and water and dried in vacuo and 3.02 g
of red powder was obtained. The powder was identified to be Compound (75)
by the measurements in accordance with NMR, IR and FD-MS (the yield:
96%). The data obtained in NMR (CDCl3, TMS) were as follows:
6.8˜7.0 (m, 2H), 7.0˜7.4 (m, 10H), 7.8˜7.9 (m, 1H),
8.0˜8.1 (m, 1H) and 8.85 (s, 1H).

Example 49

[0193]On a cleaned glass plate having an ITO electrode, Compound (TPD74)
described above was vacuum vapor deposited as the hole injecting material
and a layer having a thickness of 60 nm was formed. Then, the compound
(NPD) described above was vacuum vapor deposited as the hole transporting
material and a layer having a thickness of 20 nm was formed.

[0194]Then, the compound (Alq) described above as the light emitting
material and Compound (75) described above as the dopant were
simultaneously vapor deposited and a layer having a content of Compound
(75) of 2% by weight and a thickness of 40 nm was formed. Then, the
compound (Alq) described above was vapor deposited as the electron
injecting material and a layer having a thickness of 20 nm was formed.
After lithium fluoride was vapor deposited and a layer having a thickness
of 20 nm was formed, aluminum was vapor deposited and a layer having a
thickness of 100 nm was formed. Thus, an electrode was formed and an
organic EL device was prepared. The above layers were formed by vapor
deposition under a vacuum of 10-6 Torr while the temperature of the
substrate was kept at the room temperature. The organic EL device
exhibited a luminance of emitted light as high as 500 (cd/m2) under
application of a direct current voltage of 8 V and the emitted light was
orange light. The organic EL device exhibited a luminance of emitted
light as high as 500 (cd/m2) under application of a direct current
voltage of 8 V and the emitted light was orange light. When the organic
EL device was driven by a constant electric current at an initial
luminance of emitted light of 500 (cd/m2), the organic EL device had
a particularly long half life time, which was longer than 2,000 hours.

Example 50

[0195]An organic EL device was prepared in accordance with the same
procedures as those conducted in Example 49 except that Compound (86)
described above was used as the dopant in place of Compound (75). When
the organic EL device was driven by a constant electric current at an
initial luminance of emitted light of 500 (cd/m2), the organic EL
device had a half life time as long as 2,000 hours. The emitted light was
vermilion light.

Example 51

[0196]An organic EL device was prepared in accordance with the same
procedures as those conducted in Example 49 except that Compound (82)
described above was used as the dopant in place of Compound (75). The
organic EL device exhibited an initial luminance of emitted light of 500
(cd/m2) and the organic EL device had a half life time as long as
2,800 hours or longer when the organic EL device was driven by a constant
electric current. The emitted light was red light.

Synthesis Example 13

Compound (100)

[0197]Synthesis of Intermediate Compound H

[0198]In a 1 liter three-necked flask equipped with a condenser, 22.7 g
(0.1 mole) of 4-bromophthalic anhydride and 42.4 g (0.4 mole) of sodium
carbonate were suspended in 300 ml of water and the components were
dissolved by heating at 60° C. under an argon stream. After the
mixture was dissolved, the resulting mixture was cooled to the room
temperature. To the cooled mixture, 18.3 g (0.15 mole) of phenylboric
acid and 0.7 g (3% by mole) of palladium acetate were added and the
obtained mixture was stirred at the room temperature for one night. After
the reaction was completed, separated crystals were dissolved by adding
water. After the catalyst was removed by filtration, crystals were
precipitated by adding concentrated hydrochloric acid. The crystals were
separated by filtration and washed with water. The obtained crystals was
dissolved in ethyl acetate and the organic layer was extracted. The
extract was dried with magnesium sulfate and concentrated in vacuo using
a rotary evaporator and 23.7 g (the yield: 98%) of Intermediate Compound
H of the object compound was obtained.

[0199]Synthesis of Intermediate Compound I

[0200]In a 500 ml flask having an egg plant shape and equipped with a
condenser, 23.7 g (98 mmole) of Intermediate Compound H and 200 ml of
acetic anhydride were placed and the resulting mixture was stirred at
80° C. for 3 hours. After the reaction was completed, acetic
anhydride in an excess amount was removed by distillation and 22 g (the
yield: 10%) of Intermediate Compound I of the object compound was
obtained.

[0201]Synthesis of Intermediate Compound J

[0202]In a 500 ml three-necked flask equipped with a condenser, 7.7 g (50
mmole) of biphenyl, 13.4 g (0.1 mole) of anhydrous aluminum chloride and
200 ml of 1,2-dichloroethane were placed under an argon stream and the
resulting mixture was cooled to 0° C. To the cooled mixture, 22 g
(98 mmole) of Intermediate Compound I was slowly added and the resulting
mixture was stirred at 40° C. for 2 hours. After the reaction was
completed, ice water was added to the reaction mixture and the resulting
mixture was extracted with chloroform. The extract was dried with
magnesium sulfate and concentrated in vacuo using a rotary evaporator and
19.0 g (the yield: 100%) of Intermediate Compound J of the object
compound was obtained.

[0203]Synthesis of Intermediate Compound K

[0204]In a 500 ml flask having an egg plant shape and equipped with a
condenser, 200 ml of polyphosphoric acid was placed and heated to
150° C. Then, 19 g (50 mmole) of Intermediate Compound J was added
in small portions and the resulting mixture was stirred at the same
temperature for 3 hours. After the reaction was completed, ice water was
added to the reaction mixture and the resulting mixture was extracted
with chloroform. The extract was dried with magnesium sulfate and
concentrated in vacuo using a rotary evaporator. The obtained crude
crystals were purified in accordance with the column chromatography
(silica gel, chloroform/methanol=99/1) and 19 g (the yield: 55%) of
Intermediate Compound K of the object compound was obtained.

[0205]Synthesis of Intermediate Compound L

[0206]In a 500 ml flask having an egg plant shape and equipped with a
condenser, 19.0 g (28 mmole) of Intermediate Compound K, 0.19 g (1 mmole)
of tin chloride, 100 ml of acetic acid and 50 ml of concentrated
hydrochloric acid were placed under an argon stream and the resulting
mixture was heated under refluxing for 2 hours. After the reaction was
completed, the reaction mixture was cooled with ice water and
precipitated crystals were separated, washed with water to give 19 g (the
yield: 100%) of Intermediate Compound L of the object compound.

[0207]Synthesis of Intermediate Compound M

[0208]In a 500 ml three-necked flask equipped with a condenser, 19.0 g (28
mmole) of Intermediate Compound L, 16 g (60 mmole) of triphenylphosphine
and 200 ml of dimethylformamide were placed under an argon stream. To
this was added 9.6 g (60 mmole) of iodine dissolved in 50 ml of
dimethylformamide slowly dropwise and the resulting mixture was stirred
under heating at 200° C. for 8 hours. After the reaction was
completed, the reaction mixture was cooled with ice water and
precipitated crystals were separated. The obtained crystals were washed
with water and methanol and 6.7 g (the yield: 50%) of Intermediate
Compound M of the object compound was obtained.

[0209]Synthesis of Compound (100)

[0210]In a 200 ml three-necked flask equipped with a condenser, 4.9 g (10
mmole) of Intermediate Compound M, 5.1 g (30 mmole) of diphenylamine,
0.14 g (1.5% by mole) of tris(dibenzylideneacetone)-dipalladium, 0.91 g
(3% by mole) of tri-o-toluoylphosphine, 2.9 g (30 mmole) of sodium
t-butoxide and 50 ml of dry toluene were placed under an argon stream.
The resulting mixture was stirred overnight under heating at 100°
C. After the reaction was completed, precipitated crystals were separated
by filtration and washed with 100 ml of methanol and 4.0 g of yellow
powder was obtained. The obtained powder was identified to be Compound
(100) by the measurements in accordance with NMR, IR and FD-MS (the
yield: 60%).

[0211]The chemical structures of Intermediate Compounds and the route of
synthesis of Compound (100) are shown in the following.

##STR00076## ##STR00077##

Synthesis Example 14

Compound (101)

[0212]Synthesis of Intermediate Compound N

[0213]In a 500 ml flask having an egg plant shape and equipped with a
condenser, 12 g (50 mmole) of 2,6-dihydroxyanthraquinone, 42.5 g (0.3
mole) of methyl iodide, 17 g (0.3 mole) of potassium hydroxide and 200 ml
of dimethylsulfoxide were placed under an argon stream and the resulting
mixture was stirred at the room temperature for 2 hours. After the
reaction was completed, precipitated crystals were separated by
filtration. The obtained crystals were washed with 100 ml of methanol and
10.7 g (the yield: 80%) of Intermediate Compound N of the object compound
was obtained.

[0214]Synthesis of Intermediate Compound O

[0215]In a 500 ml three-necked flask equipped with a condenser, 10.7 g (40
mmole) of Intermediate Compound N and 200 ml of dry tetrahydrofuran were
placed under an argon stream and the resulting mixture was cooled to
-40° C. To the cooled mixture, 53 ml (80 mmole) of a 1.5 M hexane
solution of phenyllithium was added slowly dropwise. After the addition
was completed, the reaction mixture was stirred at the room temperature
for one night. After the reaction was completed, precipitated crystals
were separated by filtration and washed with 100 ml of methanol and 100
ml of acetone. The obtained crude crystals of a diol was used in the
following reaction without further purification.

[0216]In a 500 ml flask having an egg plant shape and equipped with a
condenser, the crude crystals obtained above, 100 ml of a 57% aqueous
solution of hydrogen iodide and 200 ml of acetic acid were placed and the
resulting mixture was heated under refluxing for 3 hours. After the
reaction was cooled to the room temperature, a small amount of
hypophosphorous acid was added to quench hydrogen iodide in an excess
amount. Precipitated crystals were separated by filtration and washed
with 100 ml of water, 100 ml of methanol and 100 ml of acetone,
successively, and 10.1 g (the yield: 70%) of Intermediate Compound O of
the object compound was obtained.

[0217]Synthesis of Intermediate Compound P

[0218]In a 500 ml flask having an egg plant shape and equipped with a
condenser, 10.1 g (28 mmole) of Intermediate Compound O, 7.9 g (30 mmole)
of triphenylphosphine and 200 ml of dimethylformamide were placed under
an argon stream. To the resulting mixture, 4.8 g (30 mmole) of bromine
dissolved in 50 ml of dimethylformamide was slowly added dropwise and the
obtained mixture was stirred under heating at 200° C. for 8 hours.
After the reaction was completed, the reaction mixture was cooled with
ice water and precipitated crystals were separated by filtration. The
obtained crystals were washed with water and methanol and 8.2 g (the
yield: 60%) of Intermediate Compound P of the object compound was
obtained.

[0219]Synthesis of Compound (101)

[0220]In a 200 ml three-necked flask equipped with a condenser, 4.9 g (30
mmole) of Intermediate Compound P, 5.1 g (30 mmole) of diphenylamine,
0.14 g (1.5% by mole) of tris(dibenzylideneacetone) dipalladium, 0.91 g
(3% by mole) of tri-o-toluoylphosphine, 2.9 g (30 mmole) of sodium
t-butoxide and 50 ml of dry toluene were placed under an argon stream.
The resulting mixture was stirred overnight under heating at 100°
C. After the reaction was completed, precipitated crystals were separated
by filtration and washed with 100 ml of methanol and 4.0 g of yellow
powder was obtained. The obtained powder was identified to be Compound
(101) by the measurements in accordance with NMR, IR and FD-MS (the
yield: 60%).

[0221]The chemical structures of Intermediate Compounds and the route of
synthesis of Compound (101) are shown in the following.

##STR00078##

Synthesis Example 15

Compound (93)

[0222]Synthesis of Intermediate Compound Q

[0223]In a 300 ml three-necked flask equipped with a condenser, 11.7 g (50
mmole) of 2-bromobiphenyl, 19 g (0.2 mole) of aniline, 0.69 g (1.5% by
mole) of tris(dibenzylideneacetone)dipalladium, 0.46 g (3% by mole) of
tri-o-toluoylphosphine, 7.2 g (75 mmole) of sodium t-butoxide and 100 ml
of dry toluene were placed under an argon stream. The resulting mixture
was stirred overnight under heating at 100° C. After the reaction
was completed, precipitated crystals were separated by filtration and
washed with 100 ml of methanol. The obtained crude crystals were
recrystallized from 50 ml of ethyl acetate and 9.8 g (the yield: 80%) of
Intermediate Compound Q of the object compound was obtained.

[0224]Synthesis of Compound (93)

[0225]In a 200 ml three-necked flask equipped with a condenser, 2.4 g (10
mmole) of 9,10-dibromoanthracene, 7.4 g (30 mmole) of Intermediate
Compound Q, 0.14 g (1.5% by mole) of
tris(dibenzylidene-acetone)dipalladium, 0.91 g (3% by mole) of
tri-o-toluoylphosphine, 2.9 g (30 mmole) of sodium t-butoxide and 50 ml
of dry toluene were placed under an argon stream. The resulting mixture
was stirred overnight under heating at 100° C. After the reaction
was completed, precipitated crystals were separated by filtration and
washed with 100 ml of methanol and 4.3 g of yellow powder was obtained.
The obtained powder was identified to be Compound (93) by the
measurements in accordance with NMR, IR and FD-MS (the yield: 65%).

[0226]The chemical structure of Intermediate Compound and the route of
synthesis of Compound (93) are shown in the following.

##STR00079##

Synthesis Example 16

Compound (95)

[0227]Synthesis of Intermediate Compound R

[0228]In a 1 liter three-necked flask equipped with a condenser, 34 g (0.2
mole) of 3-phenylphenol, 58 g (0.22 mmole) of triphenylphosphine and 300
ml of dimethylformamide were placed under an argon stream. To the
resulting mixture, 35 g (0.22 mmole) of bromine dissolved in 100 ml of
dimethylformamide was slowly added dropwise and the obtained mixture was
stirred at 200° C. for 8 hours After the reaction was completed,
the reaction mixture was cooled with ice water and precipitated crystals
were separated by filtration. The obtained crystals were washed with
water and methanol and 37 g (the yield: 80%) of Intermediate Compound R
of the object compound was obtained.

[0229]Synthesis of Intermediate Compound S

[0230]In a 300 ml three-necked flask equipped with a condenser, 19 g (0.2
mmole) of aniline, 0.69 g (1.5% by mole) of
tris(dibenzylidene-acetone)dipalladium, 0.46 g (3% by mole) of
tri-o-toluoylphosphine, 7.2 g (75 mmole) of sodium t-butoxide and 100 ml
of dry toluene were placed under an argon stream. The resulting mixture
was stirred overnight under heating at 100° C. After the reaction
was completed, precipitated crystals were separated by filtration and
washed with 100 ml of methanol. The obtained crude crystals were
recrystallized from 50 ml of ethyl acetate and 9.8 g (the yield: 80%) of
Intermediate Compound S of the object compound was obtained.

[0231]Synthesis of Compound (95)

[0232]In a 200 ml three-necked flask equipped with a condenser, 2.4 g (10
mmole) of 9,10-dibromoanthracene, 7.4 g (30 mmole) of Intermediate
Compound S, 0.14 g (1.5% by mole) of
tris(dibenzylidene-acetone)dipalladium, 0.91 g (3% by mole) of
tri-o-toluoylphosphine, 2.9 g (30 mmole) of sodium t-butoxide and 50 ml
of dry toluene were placed under an argon stream. The resulting mixture
was stirred overnight under heating at 100° C. After the reaction
was completed, precipitated crystals were separated by filtration and
washed with 100 ml of methanol and 4.2 g of yellow powder was obtained.
The obtained powder was identified to be Compound (95) by the
measurements in accordance with NMR, IR and FD-MS (the yield: 70%).

[0233]The chemical structures of Intermediate Compounds and the route of
synthesis of Compound (95) are shown in the following.

##STR00080##

Synthesis Example 17

Compound (104)

[0234]Synthesis of Intermediate Compound T

[0235]In a 300 ml three-necked flask equipped with a condenser, 23 g (0.1
mole) of 4-bromobiphenyl, 9.8 g (50 mmole) of aminostilbene, 0.69 g (1.5%
by mole) of tris(dibenzylideneacetone)dipalladium, 0.46 g (3% by mole) of
tri-o-toluoylphosphine, 7.2 g (75 mmole) of sodium t-butoxide and 100 ml
of dry toluene were placed under an argon stream. The resulting mixture
was stirred overnight under heating at 100° C. After the reaction
was completed, precipitated crystals were separated by filtration and
washed with 100 ml of methanol. The obtained crude crystals were
recrystallized from 50 ml of ethyl acetate and 13.9 g (the yield: 80%) of
Intermediate Compound T of the object compound was obtained.

[0236]Synthesis of Compound (104)

[0237]Into a 200 ml three-necked flask equipped with a condenser, 2.4 g
(10 mmole) of 9,10-dibromoanthracene, 7.4 g (30 mmole) of Intermediate
Compound T, 0.14 g (1.5% by mole) of tris(dibenzylidene
acetone)dipalladium, 0.91 g (3% by mole) of tri-o-toluoylphosphine, 2.9 g
(30 mmole) of sodium t-butoxide and 50 ml of dry toluene were placed
under an argon stream. The resulting mixture was stirred overnight under
heating at 100° C. After the reaction was completed, precipitated
crystals were separated by filtration and washed with 100 ml of methanol
and 4.5 g of yellow powder was obtained. The obtained powder was
identified to be Compound (104) by the measurements in accordance with
NMR, IR and FD-MS (the yield: 70%).

[0238]The chemical structure of Intermediate Compound and the route of
synthesis of Compound (104) are shown in the following.

##STR00081##

Synthesis Example 18

Compound (105)

[0239]Synthesis of Intermediate Compound U

[0240]In a 500 ml three-necked flask equipped with a condenser, 25 g (0.1
mole) of triphenylamine, 18 g (0.1 mole) of N-bromosuccimide, 0.82 g (5%
by mole) of 2,2'-azobisisobutyronitrile and 200 ml of dimethylformamide
were placed under an argon stream. The resulting mixture was stirred
under heating at 110° C. for 4 hours. After the reaction was
completed, impurities were removed by filtration and the filtrate was
concentrated in vacuo using a rotary evaporator. The obtained crude
crystals were purified in accordance with the column chromatography
(silica gel, methylene chloride) and 19 g (the yield: 60%) of
Intermediate Compound U of the object compound was obtained.

[0241]Synthesis of Intermediate Compound V

[0242]In a 1 liter three-necked flask equipped with a condenser, 1.6 g (66
mmole) of magnesium, a small piece of iodine and 100 ml of
tetrahydrofuran were placed under an argon stream. After the resulting
mixture was stirred at the room temperature for 30 minutes, 19 g (60
mole) of Intermediate Compound U dissolved in 300 ml of tetrahydrofuran
was added dropwise. After the addition was completed, the reaction
mixture was stirred under heating at 60° C. for 1 hour and a
Grignard reagent was prepared.

[0243]In a 1 liter three-necked flask equipped with a condenser, 42 g
(0.18 mmole) of 1,3-dibromobenzene, 2.1 (5% by mole) of
dichlorobis(triphenylphosphine)palladium, 6 ml (6 mmole) of a 1 M toluene
solution of diisobutylaluminum hydride and 200 ml of tetrahydrofuran were
placed under an argon stream. To the mixture, the Grignard reagent
prepared above was added dropwise and the obtained mixture was stirred
under heating for one night. After the reaction was completed, the
reaction liquid was cooled with ice water. Precipitated crystals were
separated by filtration and washed with acetone and 14 g (the yield: 60%)
of Intermediate Compound V of the object compound was obtained.

[0244]Synthesis of Compound (105)

[0245]In a 500 ml three-necked flask equipped with a condenser, 0.8 g (33
mmole) of magnesium, a small piece of iodine and 50 ml of tetrahydrofuran
were placed under an argon stream. After the resulting mixture was
stirred at the room temperature for 30 minutes, 12 g (30 mmole) of
Intermediate Compound V dissolved in 100 ml of tetrahydrofuran was added
dropwise. After the addition was completed, the reaction mixture was
stirred under heating at 60° C. for 1 hour and a Grignard reagent
was prepared.

[0246]In a 500 ml three-necked flask equipped with a condenser, 3.4 g (10
mmole) of 9,10-dibromoanthracene, 0.4 (5% by mole) of
dichlorobis(triphenylphosphine)palladium, 0.46 g (3% by mole) of
tri-o-toluoylphosphine, 1 ml (1 mmole) of a 1 M toluene solution of
diisobutylaluminum hydride and 100 ml of tetrahydrofuran were placed
under an argon stream. To the obtained mixture, the Grignard reagent
prepared above was added dropwise at the room temperature and the
resulting mixture was refluxed overnight. After the reaction was
completed, the reaction liquid was cooled with ice water. Precipitated
crystals were separated by filtration and washed with 50 ml of methanol
and 50 ml of acetone, successively, and 4.1 g of yellow powder was
obtained. The obtained powder was identified to be Compound (105) by the
measurements in accordance with NMR, IR and FD-MS (the yield: 50%).

[0247]The chemical structures of Intermediate Compounds and the route of
synthesis of Compound (105) are shown in the following.

##STR00082##

Synthesis Example 19

Compound (122)

[0248]Synthesis of Intermediate Compound W

[0249]In a 300 ml three-necked flask equipped with a condenser, 19 g (80
mmole) of 1,3-dibromobenzene, 6.5 g (20 mmole) of diphenylamine, 0.27 g
(1.5% by mole) of tris(dibenzylideneacetone)dipalladium, 0.18 g (3% by
mole) of tri-o-toluoylphosphine, 2.9 g (30 mmole) of sodium t-butoxide
and 100 ml of dry toluene were placed under an argon stream. The
resulting mixture was stirred overnight under heating at 100° C.
After the reaction was completed, precipitated crystals were separated by
filtration and washed with 100 ml of methanol. The obtained crude
crystals were recrystallized from 50 ml of ethyl acetate and 4.9 g (the
yield: 75%) of Intermediate Compound W of the object compound was
obtained.

[0250]Synthesis of Compound (122)

[0251]In a 300 ml three-necked flask equipped with a condenser, 0.5 g (20
mmole) of magnesium, a small piece of iodine and 50 ml of tetrahydrofuran
were placed under an argon stream. After the resulting mixture was
stirred at the room temperature for 30 minutes, 4.9 g (15 mmole) of
Intermediate Compound W dissolved in 100 ml of tetrahydrofuran was added
dropwise. After the addition was completed, the reaction mixture was
stirred under heating at 60° C. for 1 hour and a Grignard reagent
was prepared.

[0252]In a 500 ml three-necked flask equipped with a condenser, 1.7 g (5
mmole) of 9,10-dibromoanthracene, 0.2 g (5% by mole) of
dichlorobis(triphenylphosphine)palladium, 0.5 ml (0.5 mmole) of a 1 M
toluene solution of diisobutylaluminum hydride and 100 ml of
tetrahydrofuran were placed under an argon stream. To the mixture, the
Grignard reagent prepared above was added dropwise at the room
temperature and the resulting mixture was stirred overnight under
heating. After the reaction was completed, the reaction liquid was cooled
with ice water. Precipitated crystals were separated by filtration and
washed with 50 ml of methanol and 50 ml of acetone, successively, and 1.7
g of yellow powder was obtained. The obtained powder was identified to be
Compound (122) by the measurements in accordance with NMR, IR and FD-MS
(the yield: 50%).

[0253]The chemical structure of Intermediate Compound and the route of
synthesis of Compound (122) are shown in the following.

##STR00083##

Synthesis Example 20

Compound (123)

[0254]Synthesis of Intermediate Compound X

[0255]In a 300 ml three-necked flask equipped with a condenser, 16 g (0.1
mole) of bromobenzene, 9.8 g (50 mmole) of aminostilbene, 0.69 g (1.5% by
mole) of tris(dibenzylideneacetone)dipalladium, 0.46 g (3% by mole) of
tri-o-toluoylphosphine, 7.2 g (75 mmole) of sodium t-butoxide and 100 ml
of dry toluene were placed under an argon stream. The resulting mixture
was stirred overnight under heating at 100° C. After the reaction
was completed, precipitated crystals were separated by filtration and
washed with 100 ml of methanol. The obtained crude crystals were
recrystallized from 50 ml of ethyl acetate and 11 g (the yield: 80%) of
Intermediate Compound X of the object compound was obtained.

[0256]Synthesis of Intermediate Compound Y

[0257]In a 500 ml three-necked flask equipped with a condenser, 38 g (0.16
mole) of bromobenzene, 11 g (40 mmole) of Intermediate Compound X, 0.55 g
(1.5% by mole) of tris(dibenzylideneacetone)-dipalladium, 0.37 g (3% by
mole) of tri-o-toluoylphosphine, 5.8 g (60 mmole) of sodium t-butoxide
and 300 ml of dry toluene were placed under an argon stream. The
resulting mixture was stirred overnight under heating at 120° C.
After the reaction was completed, precipitated crystals were separated by
filtration and washed with 100 ml of methanol. The obtained crude
crystals were recrystallized from 50 ml of ethyl acetate and 13 g (the
yield: 75%) of Intermediate Compound Y of the object compound was
obtained.

[0258]Synthesis of Compound (123)

[0259]In a 300 ml three-necked flask equipped with a condenser, 0.97 g (40
mmole) of magnesium, a small piece of iodine and 50 ml of tetrahydrofuran
were placed under an argon stream. After the resulting mixture was
stirred at the room temperature for 30 minutes, 12 g (30 mole) of
Intermediate Compound Y dissolved in 100 ml of tetrahydrofuran was added
dropwise. After the addition was completed, the reaction mixture was
stirred under heating at 60° C. for 1 hour and a Grignard reagent
was prepared.

[0260]In a 500 ml three-necked flask equipped with a condenser, 3.4 g (10
mmole) of 9,10-dibromoanthracene, 0.4 g (5% by mole) of
dichlorobis(triphenylphosphine)palladium, 1 ml (1 mmole) of a 1 M toluene
solution of diisobutylaluminum hydride and 100 ml of tetrahydrofuran were
placed under an argon stream. To the obtained mixture, the Grignard
reagent prepared above was added dropwise at the room temperature and the
resulting mixture was refluxed overnight. After the reaction was
completed, the reaction liquid was cooled with ice water. Precipitated
crystals were separated by filtration and washed with 50 ml of methanol
and 50 ml of acetone, successively, and 5.4 g of yellow powder was
obtained. The obtained powder was identified to be Compound (123) by the
measurements in accordance with NMR, IR and FD-MS (the yield: 50%).

[0261]The chemical structures of Intermediate Compounds and the route of
synthesis of Compound (123) are shown in the following.

##STR00084##

Synthesis Example 21

Compound (124)

[0262]Synthesis of Compound (124)

[0263]In a 500 ml three-necked flask equipped with a condenser, 2.5 g (5
mmole) of 10,10'-dibromo-9,9'-bianthryl, 0.2 g (5% by mole) of
dichlorobis(triphenylphosphine)palladium, 0.5 ml (0.5 mmole) of a 1 M
toluene solution of diisobutylaluminum hydride and 100 ml of
tetrahydrofuran were placed under an argon stream. To the mixture, the
Grignard reagent prepared in Synthesis Example 19 was added dropwise at
the room temperature and the resulting mixture was refluxed overnight.
After the reaction was completed, the reaction liquid was cooled with ice
water. Precipitated crystals were separated by filtration and washed with
50 ml of methanol and 50 ml of acetone, successively, and 2.0 g of yellow
powder was obtained. The obtained powder was identified to be Compound
(124) by the measurements in accordance with NMR, IR and FD-MS (the
yield: 60%).

[0264]The route of synthesis of Compound (124) is shown in the following.

##STR00085##

Synthesis Example 22

Compound (125)

[0265]Synthesis of Compound (125)

[0266]In a 500 ml three-necked flask equipped with a condenser, 1.9 g (5
mmole) of 6,12-dibromochrysene, 0.2 g (5% by mole) of
dichlorobis(triphenylphosphine)palladium, 0.5 ml (0.5 mmole) of a 1 M
toluene solution of diisobutylaluminum hydride and 100 ml of
tetrahydrofuran were placed under an argon stream. To the mixture, the
Grignard reagent prepared in Synthesis Example 19 was added dropwise at
the room temperature and the resulting mixture was stirred under heating
overnight. After the reaction was completed, the reaction liquid was
cooled with ice water. Precipitated crystals were separated by filtration
and washed with 50 ml of methanol and 50 ml of acetone, successively, and
2.1 g of yellow powder was obtained. The obtained powder was identified
to be Compound (125) by the measurements in accordance with NMR, IR and
FD-MS (the yield: 60%).

[0267]The route of synthesis of Compound (125) is shown in the following.

##STR00086##

Synthesis Example 23

Compound (126)

[0268]Synthesis of Compound (126)

[0269]In a 500 ml three-necked flask equipped with a condenser, 1.9 g (5
mmole) of 5,12-dibromonaphthacene, 0.2 g (5% by mole) of
dichlorobis(triphenylphosphine)palladium, 0.5 ml (0.5 mmole) of a 1 M
toluene solution of diisobutylaluminum hydride and 100 ml of
tetrahydrofuran were placed under an argon stream. To the mixture, the
Grignard reagent prepared in Synthesis Example 19 was added dropwise at
the room temperature and the resulting mixture was stirred under heating
overnight. After the reaction was completed, the reaction liquid was
cooled with ice water. Precipitated crystals were separated by filtration
and washed with 50 ml of methanol and 50 ml of acetone, successively, and
2.1 g of yellow powder was obtained. The obtained powder was identified
to be Compound (126) by the measurements in accordance with NMR, IR and
FD-MS (the yield: 60%).

[0270]The route of synthesis of Compound (126) is shown in the following.

##STR00087##

Example 52

[0271]On a glass substrate having a size of 25 mm×75 mm×1.1
mm, a transparent anode of a film of indium tin oxide having a thickness
of 100 nm was formed and cleaned for 10 minutes by using ultraviolet
light and ozone in combination.

[0272]This glass substrate was placed into an apparatus for vacuum vapor
deposition (manufactured by NIPPON SHINKUU GIJUTU Co., Ltd.) and the
pressure was reduced to about 10-4 Pa. TPD74 described above was
vapor deposited at a speed of 0.2 nm/second and a layer having a
thickness of 60 nm was formed. Then, TPD78 having the structure shown
below was vapor deposited at a speed of 0.2 nm/second and a layer having
a thickness of 20 nm was formed.

[0273]On the layer formed above, DPVDPAN having the structure shown below
and Compound (100) described above as the light emitting material were
simultaneously vapor deposited and a light emitting layer having a
thickness of 40 nm was formed. The speed of vapor deposition of DPVDPAN
was 0.4 nm/second and the speed of vapor deposition of Compound (100) was
0.01 nm/second. On the layer formed above, Alq described above was vapor
deposited at a speed of 0.2 nm/second. Finally, aluminum and lithium were
vapor deposited simultaneously and a cathode having a thickness of 150 nm
was formed. Thus, an organic EL device was obtained. The speed of vapor
deposition of aluminum was 1 nm/second and the speed of vapor deposition
of lithium was 0.004 nm/second.

##STR00088##

[0274]The properties of the obtained organic EL device were evaluated.
Luminance of emitted light at the voltage shown in Table 4 was measured
and the efficiency of light emission was calculated. The color of emitted
light was observed. The organic EL device was driven by a constant
electric current under a nitrogen stream at an initial luminance of
emitted light of 500 (cd/m2) and the half life time which was the
time before the luminance decreases to 250 (cd/m2) was measured. The
results are shown in Table 4.

Examples 53 to 62

[0275]Organic EL devices were prepared in accordance with the same
procedures as those conducted in Example 52 except that the compounds
shown in Table 4 were used as the light emitting material in place of
Compound (100) and the properties were evaluated. The results are shown
in Table 4.

Comparative Example 8

[0276]An organic EL devices was prepared in accordance with the same
procedures as those conducted in Example 52 except that the diamine
compound shown below was used as the light emitting material in place of
Compound (100) and the properties were evaluated. The results are shown
in Table 4.

[0277]As shown in Table 4, the organic EL devices of Examples 52 to 62 in
which the compounds represented by general formulae [9] and [10] of the
present invention were used as the light emitting material or the hole
transporting material exhibited more excellent luminance of emitted light
and efficiencies of light emission and longer lives in comparison with
the organic EL device of Comparative Example 8 in which the diamine
compound was used.

Synthesis Example 24

Compound A

[0278]Synthesis of Intermediate Compound A

[0279]In a 500 ml three-necked flask, 50 g (0.27 mole) of
p-bromobenzaldehyde, 50 g (0.22 mmole) of diethyl benzylphosphonate and
200 ml of dimethylsulfoxide were placed under an argon stream. To this
was added 30 g (0.27 mole) of potassium t-butoxide in small portions. The
resulting mixture was stirred overnight at the room temperature. After
the reaction was completed, the reaction liquid was poured into 500 ml of
water and extracted with ethyl acetate. The extract was dried with
magnesium sulfate and concentrated in vacuo using a rotary evaporator.
The obtained crude crystals were recrystallized from 100 ml of ethyl
acetate and 46 g (the yield: 81%) of Intermediate Compound A was
obtained.

[0280]Synthesis of Intermediate Compound B

[0281]Into a 300 ml three-necked flask equipped with a condenser, 10 g (38
mmole) of Intermediate Compound A, 14 g (150 mmole) of aniline, 0.53 g
(1.5% by mole) of tris(dibenzylideneacetone)dipalladium, 0.35 g (3% by
mole) of tri-o-toluoylphosphine, 7.4 g (77 mole) of sodium t-butoxide and
100 ml of dry toluene were placed under an argon stream. The resulting
mixture was stirred overnight under heating at 100° C. After the
reaction was completed, precipitated crystals were separated by
filtration and washed with 100 ml of methanol. The obtained crude
crystals were recrystallized from 50 ml of ethyl acetate and 7.7 g (the
yield: 73%) of Intermediate Compound B was obtained.

[0282]Synthesis of Intermediate Compound C

[0283]In a 100 ml flask having an egg plant shape and equipped with a
condenser, 12.5 g (50 mmole) of 4-bromobenzyl bromide and 12.5 (75 mmole)
of triethyl phosphite were placed. The resulting mixture was stirred
under heating at 100° C. for 7 hours. After the reaction was
completed, triethyl phosphite in an excess amount was removed by
distillation in vacuo and 15.4 g of Intermediate Compound C was obtained.
Intermediate Compound C was used in the following reaction without
further purification.

[0284]Synthesis of Intermediate Compound D

[0285]In a 300 ml three-necked flask, 9.2 g (50 mmole) of
p-bromobenzaldehyde, 15.4 g (50 mmole) of Intermediate Compound C and 100
ml of dimethylsulfoxide were placed under an argon stream. To this was
added 6.7 g (60 mmole) of potassium t-butoxide in small portions and the
resulting mixture was stirred overnight at the room temperature. After
the reaction was completed, the reaction liquid was poured into 200 ml of
water and extracted with ethyl acetate. The extract was dried with
magnesium sulfate and concentrated in vacuo using a rotary evaporator.
The obtained crystals were washed with 100 ml of methanol and 13 g (the
yield: 77%) of Intermediate compound D was obtained.

[0286]Synthesis of Compound a

[0287]In a 200 ml three-necked flask equipped with a condenser, 4 g (15
mmole) of Intermediate Compound B, 2 g (6 mmole) of Intermediate Compound
D, 0.16 g (3% by mole) of tris(dibenzylideneacetone)dipalladium, 0.22 g
(6% by mole) of (S)-BINAP, 1.4 g (15 mmole) of sodium t-butoxide and 50
ml of dry toluene were placed under an argon stream. The resulting
mixture was stirred overnight under heating at 100° C. After the
reaction was completed, precipitated crystals were separated by
filtration, washed with methanol and dried by heating at 60° C.
for one night. The obtained crude crystals were purified in accordance
with the column chromatography (silica gel, hexane/toluene=8/2) and 1.4 g
of yellow powder was obtained. The obtained powder was identified to be
Compound a by the measurements in accordance with NMR, IR and FD-MS (the
field desorption mass spectroscopy) (the yield: 32%, in 1HNMR
(90 Hz): δ 7.0˜7.4 ppm (42H, m)). The NMR chart of Compound a
is shown in FIG. 1.

[0288]The chemical reactions to obtain Compound a are shown in the
following:

##STR00090##

Synthesis Example 25

Compound B

[0289]Synthesis of Intermediate Compound E

[0290]In a 300 ml three-necked flask, 6 g (50 mmole) of p-tolualdehyde,
15.4 g (50 mmole) of Intermediate Compound C and 100 ml of
dimethylsulfoxide were placed under an argon stream. To this was added
6.7 g (60 mmole) of potassium t-butoxide in small portions and the
resulting mixture was stirred overnight at the room temperature. After
the reaction was completed, the reaction liquid was poured into 200 ml of
water and extracted with ethyl acetate. The extract was dried with
magnesium sulfate and concentrated in vacuo using a rotary evaporator.
The obtained crystals were washed with 100 ml of methanol and 9.2 g (the
yield: 67%) of Intermediate Compound E was obtained.

[0291]Synthesis of Compound b

[0292]In a 200 ml three-necked flask equipped with a condenser, 4 g (15
mmole) of Intermediate Compound E, 2 g (6 mmole) of
N,N'-diphenylbenzidine, 0.16 g (3% by mole) of tris(dibenzylideneacetone)
dipalladium, 0.22 g (6% by mole) of (S)-BINAP, 1.4 g (15 mmole) of sodium
t-butoxide and 50 ml of dry toluene were placed under an argon stream.
The resulting mixture was stirred overnight under heating at 100°
C. After the reaction was completed, precipitated crystals were separated
by filtration, washed with methanol and dried by heating at 60° C.
for one night. The obtained crude crystals were purified in accordance
with the column chromatography (silica gel, hexane/toluene=8/2) and 2.5 g
of yellow powder was obtained. The obtained powder was identified to be
Compound b by the measurements in accordance with NMR, IR and FD-MS (the
yield: 58%, in 1HNMR (90 Hz): δ 7.0˜7.4 ppm (40H,
m), δ 2.34 ppm (6H, s)). The NMR chart of Compound b is shown in
FIG. 2.

[0293]The chemical reactions to obtain Compound b are shown in the
following:

##STR00091##

Synthesis Example 26

Compound C

[0294]Synthesis of Compound c

[0295]In a 200 ml three-necked flask equipped with a condenser, 4 g (15
mmole) of Intermediate Compound B, 1.7 g (6 mmole) of
1,4-dibromonaphthalene, 0.16 g (3% by mole) of tris(dibenzylideneacetone)
dipalladium, 0.22 g (6% by mole) of (S)-BINAP, 1.4 g (15 mmole) of sodium
t-butoxide and 50 ml of dry toluene were placed under an argon stream.
The resulting mixture was stirred over night under heating at 100°
C. After the reaction was completed, precipitated crystals were separated
by filtration, washed with methanol and dried by heating at 60° C.
for one night. The obtained crude crystals were purified in accordance
with the column chromatography (silica gel, hexane/toluene=8/2) and 2.0 g
of yellow powder was obtained. The obtained powder was identified to be
Compound c by the measurements in accordance with NMR, IR and FD-MS (the
yield: 50%, in 1HNMR (90 Hz): δ 7.0˜7.4 ppm (68H,
m)).

[0296]The chemical reaction to obtain Compound c is shown in the
following:

##STR00092##

Synthesis Example 27

Compound D

[0297]Synthesis of Compound d

[0298]In a 200 ml three-necked flask equipped with a condenser, 4 g (15
mmole) of Intermediate Compound B, 2 g (6 mmole) of
9,10-dibromoanthracene, 0.16 g (3% by mole) of tris(dibenzylideneacetone)
dipalladium, 0.07 g (6% by mole) of tri-t-butylphosphine, 1.4 g (15
mmole) of sodium t-butoxide and 50 ml of dry toluene were placed under an
argon stream. The resulting mixture was stirred overnight under heating
at 100° C. After the reaction was completed, precipitated crystals
were separated by filtration, washed with methanol and dried by heating
at 60° C. for one night. The obtained crude crystals were purified
in accordance with the column chromatography (silica gel,
hexane/toluene=8/2) and 1.9 g of yellow powder was obtained. The obtained
powder was identified to be Compound d by the measurements in accordance
with NMR, IR and FD-MS (the yield: 44%, in 1HNMR (90 Hz):
δ 7.0˜7.4 ppm (40H, m)).

[0299]The chemical reaction to obtain Compound d is shown in the
following:

##STR00093##

Synthesis Example 28

Compound E

[0300]Synthesis of Intermediate Compound E

[0301]In a 300 ml three-necked flask, 10.4 g (50 mmole) of
trans-4-stilbenealdehyde, 15.4 g (50 mmole) of Intermediate Compound C
and 100 ml of dimethylsulfoxide were placed under an argon stream. To
this was added 6.7 g (60 mmole) of potassium t-butoxide in small portions
and the resulting mixture was stirred overnight at the room temperature.
After the reaction was completed, the reaction liquid was poured into 200
ml of water and extracted with ethyl acetate. The extract was dried with
magnesium sulfate and concentrated in vacuo using a rotary evaporator.
The obtained crystals were washed with 100 ml of methanol and 12.5 g (the
yield: 69%) of Intermediate Compound F was obtained.

[0302]Synthesis of Compound e

[0303]In a 200 ml three-necked flask equipped with a condenser, 5.4 g (15
mmole) of Intermediate Compound F, 2 g (6 mmole) of
N,N'-diphenylbenzidine, 0.16 g (3% by mole) of tris(dibenzylideneacetone)
dipalladium, 0.11 g (6% by mole) of tri-o-toluoylphosphine, 1.4 g (15
mmole) of sodium t-butoxide and 50 ml of dry toluene were placed under an
argon stream. The resulting mixture was stirred overnight under heating
at 100° C. After the reaction was completed, precipitated crystals
were separated by filtration, washed with methanol and dried by heating
at 60° C. for one night. The obtained crude crystals were purified
in accordance with the column chromatography (silica gel,
hexane/toluene=6/4) and 1.0 g of yellow powder was obtained. The obtained
powder was identified to be Compound e by the measurements in accordance
with NMR, IR and FD-MS (the yield: 19%, in 1HNMR (90 Hz):
δ 7.0˜7.5 ppm (52H, m)). The NMR chart of Compound e is shown
in FIG. 3.

[0304]The chemical reactions to obtain Compound e are shown in the
following:

##STR00094##

[0305]Synthesis of Compound f

[0306]In a 200 ml three-necked flask equipped with a condenser, 7.8 g (30
mmole) of Intermediate Compound A, 1.7 g (6 mmole) of 4,4'
diaminostilbene carbon dioxide, 0.16 g (3% by mole) of tris(dibenzylidene
acetone)dipalladium, 0.22 g (6% by mole) of (S)-BINAP, 9.6 g (0.1 mole)
of sodium t-butoxide and 50 ml of dry toluene were placed under an argon
stream. The resulting mixture was stirred overnight under heating at
100° C. After the reaction was completed, precipitated crystals
were separated by filtration, washed with methanol and dried by heating
at 60° C. for one night. The obtained crude crystals were purified
in accordance with the column chromatography (silica gel,
hexane/toluene=6/4) and 2.0 g of yellow powder was obtained. The obtained
powder was identified to be Compound f by the measurements in accordance
with NMR, IR and FD-MS (the yield: 36%, in 1HNMR (90 Hz):
δ 7.0˜7.5 ppm (54H, m)).

[0307]The chemical reaction to obtain Compound f is shown in the
following:

##STR00095##

Example 63

[0308]On a cleaned glass plate having an ITO electrode, TPD74 described
above was vacuum vapor deposited as the hole injecting material and a
layer having a thickness of 60 nm was formed.

[0309]Then, NPD described above was vacuum vapor deposited as the hole
transporting material and a layer having a thickness of 20 nm was formed.

[0310]Subsequently, as the light emitting materials,
4,4'-bis(2,2-diphenylvinyl)biphenyl (DPVBi) which is a stilbene
derivative and Compound a described above were simultaneously vapor
deposited and a layer having a content of Compound a of 2% by weight and
a thickness of 40 nm was formed. Compound a works as a fluorescent dopant
or the light emitting center. On the layer formed above, Alq described
above was vapor deposited as the electron injecting material and a layer
having a thickness of 20 nm was formed. After lithium fluoride was vapor
deposited and a layer having a thickness of 0.5 nm was formed, aluminum
was vapor deposited and a layer having a thickness of 100 nm was formed.
Thus, an electrode was formed and an organic EL device was obtained. The
layers were vapor deposited in a vacuum of 10-6 Torr while the
substrate was kept at the room temperature. The device exhibited a
luminance of emitted light of 100 (cd/m2) and an efficiency of light
emission of 2.1 (lm/W) under application of a direct current voltage of 6
V. The color coordinate was (0.146, 0.140) and blue light of a high
purity could be emitted. When the organic EL device was driven by a
constant electric current at an initial luminance of emitted light of 200
(cd/m2), the half life time was as long as 2,000 hours. The
properties of light emission are shown in Table 5.

[0311]The energy gap of Compound a was 2.78 eV and the energy gap of DPVBi
was 3.0 eV.

Example 64

[0312]An organic EL device was prepared in accordance with the same
procedures as those conducted in Example 63 except that Compound b was
used as the dopant or the light emitting center. The device exhibited a
luminance of emitted light of 110 (cd/m2) and an efficiency of light
emission of 1.3 (lm/W) under application of a direct current voltage of 6
V. The color coordinate was (0.152, 0.163) and blue light of a high
purity could be emitted. When the organic EL device was driven by a
constant electric current at an initial luminance of emitted light of 200
(cd/m2), the half life time was as long as 1,500 hours. The
properties of light emission are shown in Table 5.

[0313]The energy gap of Compound b was 2.90 eV and the energy gap of DPVBi
was 3.0 eV.

Example 65

[0314]An organic EL device was prepared in accordance with the same
procedures as those conducted in Example 63 except that Compound c was
used as the dopant or the light emitting center. The device exhibited a
luminance of emitted light of 130 (cd/m2) and an efficiency of light
emission of 2.1 (lm/W) under application of a direct current voltage of 6
V. The color coordinate was (0.162, 0.181) and blue light of a high
purity could be emitted. When the organic EL device was driven by a
constant electric current at an initial luminance of emitted light of 200
(cd/m2), the half life time was as long as 2,800 hours. The
properties of light emission are shown in Table 5.

[0315]The energy gap of Compound b was 2.83 eV and the energy gap of DPVBi
was 3.0 eV.

Example 66

[0316]An organic EL device was prepared in accordance with the same
procedures as those conducted in Example 63 except that Compound d was
used as the dopant or the light emitting center. The device exhibited a
luminance of emitted light of 300 (cd/m2) and an efficiency of light
emission of 4.6 (lm/W) under application of a direct current voltage of 6
V. Light of green color could be emitted with a high efficiency. When the
organic EL device was driven by a constant electric current at an initial
luminance of emitted light of 200 (cd/m2), the half life time was as
long as 3,400 hours. The properties of light emission are shown in Table
5.

[0317]The energy gap of Compound d was 2.78 eV and the energy gap of DPVBi
was 3.0 eV.

Comparative Example 9

[0318]An organic EL device was prepared in accordance with the same
procedures as those conducted in Example 63 except that the following
compound (TPD):

##STR00096##

was used as the dopant or the light emitting center. The device exhibited
a luminance of emitted light of 60 (cd/m2) and an efficiency of
light emission of 0.7 (lm/W) under application of a direct current
voltage of 5 V. Sufficient properties could not be obtained. TPD did not
work as the light emitting center and light emitted from DPVTP was
obtained. When the organic EL device was driven by a constant electric
current at an initial luminance of emitted light of 200 (cd/m2), the
half life time was as short as 100 hours. The properties of light
emission are shown in Table 5.

[0319]The energy gap of TPD was 3.10 eV and the energy gap of DPVBi was
3.0 eV.

Comparative Example 10

[0320]An organic EL device was prepared in accordance with the same
procedures as those conducted in Example 63 except that Compound a
described above was used as the dopant or the light emitting material and
the compound Alq was used as the light emitting material. The device
exhibited a luminance of emitted light of 210 (cd/m2) and an
efficiency of light emission of 1.3 (lm/W) under application of a direct
current voltage of 6 V. However, light of pink color from Alq alone was
obtained. When the organic EL device was driven by a constant electric
current at an initial luminance of emitted light of 200 (cd/m2), the
half life time was as short as 200 hours. The properties of light
emission are shown in Table 5. Compound a did not work as the light
emitting center.

[0321]The energy gap of Compound a was 2.95 eV and the energy gap of Alq
was 2.7 eV.

Comparative Example 11

[0322]An organic EL device was prepared in accordance with the same
procedures as those conducted in Example 63 except that no dopant or
light emitting material was used and Compound c described above was used
as the single light emitting material. The device exhibited luminance of
emitted light of 40 (cd/m2) and an efficiency of light emission of
0.9 (lm/W) under application of a direct current voltage of 6 V.
Sufficient properties could not be obtained. When the organic EL device
was driven by a constant electric current at an initial luminance of
emitted light of 200 (cd/m2), the half life time was as short as 180
hours. The properties of light emission are shown in Table 5.

[0324]As shown in Table 5, the organic EL devices of Examples 63 to 66 in
which a small amount (1 to 20% by weight) of a compound represented by
general formula [1] was added to the host material as the dopant or the
light emitting center exhibited higher efficiencies of light emission and
much longer lives in comparison with the organic EL devices of
Comparative Examples 9 to 11.

INDUSTRIAL APPLICABILITY

[0325]The organic EL devices of the present invention in which the
materials for organic EL devices represented by general formulae [1], [3]
to [6] and [9] to [10] described above are used as the light emitting
material, the hole injecting material, the hole transporting material or
the doping material exhibit luminances of light emission sufficient for
practical use and high efficiencies of light emission under application
of a low voltage, have long lives because the decrease in the properties
after use for a long time is suppressed and show no deterioration in the
properties in the environment of high temperatures due to excellent heat
resistance.

[0326]The organic EL devices described above in which the materials for
organic EL devices represented by general formulae [7] and [8] are used
as the light emitting material, the hole injecting material, the hole
transporting material or the doping material exhibit, in the region of
yellow color and orange to red color, luminances of light emission
sufficient for practical use and high efficiencies of light emission
under application of a low voltage and have long life times because the
decrease in the properties after use for a long time is suppressed.

[0327]The organic EL devices in which the material for organic EL devices
comprising the compound represented by general formula [11] of the
present invention or the novel compound represented by general formula
[11'] of the present invention is used as the dopant or the light
emitting center exhibit luminances of emitted light sufficient for
practical use under application of a low voltage and high efficiencies of
light emission and have long lives because the decrease in the properties
after use for a long time is suppressed.

[0328]By producing materials for organic EL devices in accordance with the
process of the present invention, materials for organic EL devices
exhibiting a high efficiency of light emission, having a long life,
showing high activity and containing little impurities can be produced in
a high yield.

[0329]Obviously, numerous modifications and variations of the present
invention are possible in light of the above teachings. It is therefore
to be understood that within the scope of the appended claims, the
invention may be practiced otherwise than as specifically described
herein.